JP5962546B2 - Radiation sensitive resin composition, cured film, method for forming the same, and display element - Google Patents
Radiation sensitive resin composition, cured film, method for forming the same, and display element Download PDFInfo
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- JP5962546B2 JP5962546B2 JP2013044780A JP2013044780A JP5962546B2 JP 5962546 B2 JP5962546 B2 JP 5962546B2 JP 2013044780 A JP2013044780 A JP 2013044780A JP 2013044780 A JP2013044780 A JP 2013044780A JP 5962546 B2 JP5962546 B2 JP 5962546B2
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- resin composition
- radiation
- compound
- sensitive resin
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- 230000005855 radiation Effects 0.000 title claims description 89
- 239000011342 resin composition Substances 0.000 title claims description 71
- 238000000034 method Methods 0.000 title claims description 38
- -1 acryloyloxy group Chemical group 0.000 claims description 153
- 229920000642 polymer Polymers 0.000 claims description 90
- 150000001875 compounds Chemical class 0.000 claims description 86
- 239000000758 substrate Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 239000011248 coating agent Substances 0.000 claims description 27
- 238000000576 coating method Methods 0.000 claims description 27
- 230000015572 biosynthetic process Effects 0.000 claims description 26
- 239000003963 antioxidant agent Substances 0.000 claims description 14
- 230000003078 antioxidant effect Effects 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000000466 oxiranyl group Chemical group 0.000 claims description 13
- 125000002723 alicyclic group Chemical group 0.000 claims description 12
- 125000003566 oxetanyl group Chemical group 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 150000004292 cyclic ethers Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 3
- 239000010408 film Substances 0.000 description 119
- 239000000243 solution Substances 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 239000004973 liquid crystal related substance Substances 0.000 description 18
- 230000035945 sensitivity Effects 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 14
- 239000003822 epoxy resin Substances 0.000 description 14
- 229920000647 polyepoxide Polymers 0.000 description 14
- 150000007514 bases Chemical class 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 238000011161 development Methods 0.000 description 12
- 230000018109 developmental process Effects 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229920002223 polystyrene Polymers 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 239000011229 interlayer Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- DSVYZVHQBQDCGE-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethylcarbamoylamino)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCNC(=O)NCCOC(=O)C=C DSVYZVHQBQDCGE-UHFFFAOYSA-N 0.000 description 6
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- DYRMLWPTRUYYPH-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethylcarbamoylamino]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(=O)NCCOC(=O)C(C)=C DYRMLWPTRUYYPH-UHFFFAOYSA-N 0.000 description 5
- LCFAUVOBPRLSCP-UHFFFAOYSA-N C(C(=C)C)(=O)OC(CNC(=O)NCC(OCC)OC(C(=C)C)=O)OCC Chemical compound C(C(=C)C)(=O)OC(CNC(=O)NCC(OCC)OC(C(=C)C)=O)OCC LCFAUVOBPRLSCP-UHFFFAOYSA-N 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical class SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 210000002858 crystal cell Anatomy 0.000 description 5
- 230000007547 defect Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 125000006850 spacer group Chemical group 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 4
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical class C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- QHGUPRQTQITEPO-UHFFFAOYSA-N oxan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCO1 QHGUPRQTQITEPO-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 3
- ZYVXFNCWRJNIQJ-UHFFFAOYSA-M 1-(4,7-dibutoxynaphthalen-1-yl)thiolan-1-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC(OCCCC)=CC=C2C(OCCCC)=CC=C1[S+]1CCCC1 ZYVXFNCWRJNIQJ-UHFFFAOYSA-M 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 3
- 230000003321 amplification Effects 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 3
- IWPATTDMSUYMJV-UHFFFAOYSA-N butyl 2-methoxyacetate Chemical compound CCCCOC(=O)COC IWPATTDMSUYMJV-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003199 nucleic acid amplification method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical class C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- KQDCUEMOGIRBNY-UHFFFAOYSA-N (2,5-dioxo-3,4-diphenylpyrrol-1-yl) 4-fluorobenzenesulfonate Chemical compound C1=CC(F)=CC=C1S(=O)(=O)ON1C(=O)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C1=O KQDCUEMOGIRBNY-UHFFFAOYSA-N 0.000 description 2
- RSHKWPIEJYAPCL-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(CC)COC1 RSHKWPIEJYAPCL-UHFFFAOYSA-N 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- XXNDEOCNKXHSGK-UHFFFAOYSA-N 1-butoxyethyl 2-methylprop-2-enoate Chemical compound CCCCOC(C)OC(=O)C(C)=C XXNDEOCNKXHSGK-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
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- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- CKRLZVYBDRHVQG-UHFFFAOYSA-N tris(2,6-difluorophenyl) borate Chemical compound FC1=CC=CC(F)=C1OB(OC=1C(=CC=CC=1F)F)OC1=C(F)C=CC=C1F CKRLZVYBDRHVQG-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
Description
本発明は、感放射線性樹脂組成物、硬化膜、その形成方法、及び表示素子に関する。 The present invention relates to a radiation-sensitive resin composition, a cured film, a method for forming the same, and a display element.
薄膜トランジスタ型液晶表示素子等の電子部品には、一般に層状に配置される配線の間を絶縁するために層間絶縁膜が設けられており、有機エレクトロルミネッセンス素子にも半導体素子の上部を平坦化し、その平坦化膜の上に電極と発光層が積層するために平坦化膜が設けられている。
例えば、薄膜トランジスタ型液晶表示素子は、層間絶縁膜の上に透明電極膜を形成し、さらにその上に液晶配向膜を形成する工程を経て製造される。そのため層間絶縁膜には、透明電極膜の形成工程において高温条件にさらされたり、電極のパターン形成に使用されるレジストの剥離液に曝されることとなるため、これらに対する十分な耐熱性及び耐溶媒性が必要となる。
In an electronic component such as a thin film transistor type liquid crystal display element, an interlayer insulating film is generally provided to insulate between wirings arranged in layers, and the upper part of a semiconductor element is flattened in an organic electroluminescence element. A flattening film is provided for stacking the electrode and the light emitting layer on the flattening film.
For example, a thin film transistor type liquid crystal display element is manufactured through a process of forming a transparent electrode film on an interlayer insulating film and further forming a liquid crystal alignment film thereon. For this reason, the interlayer insulating film is exposed to high temperature conditions in the transparent electrode film formation process or to a resist stripping solution used for electrode pattern formation. Solvent properties are required.
従来の液晶表示素子用の層間絶縁膜は、パターンニング性能の観点からナフトキノンジアジド等の酸発生剤を用いたポジ型感放射線性樹脂組成物が用いられている(例えば、特開2001−354822号公報参照)。
近年、ナフトキノンジアジド等の酸発生剤を用いたポジ型感放射線性樹脂組成物よりも高い感度で表示素子用の硬化膜の形成することを目的として、例えば特開2004−4669号公報には、架橋剤、酸発生剤、及びそれ自体はアルカリ水溶液に不溶又は難溶であるが、酸の作用により解裂しうる保護基を有し、該保護基が解裂した後はアルカリ水溶液に可溶性となる樹脂を含有することを特徴とするポジ型化学増幅材料が提案されている。また特開2004−264623号公報、特開2008−304902号公報等には、アセタール構造及び/又はケタール構造並びにエポキシ基を含有する樹脂と酸発生剤とを含有することを特徴とするポジ型感放射線性組成物が提案されている。
As a conventional interlayer insulating film for liquid crystal display elements, a positive radiation sensitive resin composition using an acid generator such as naphthoquinonediazide is used from the viewpoint of patterning performance (for example, JP-A-2001-354822). See the official gazette).
Recently, for the purpose of forming a cured film for a display element with higher sensitivity than a positive radiation-sensitive resin composition using an acid generator such as naphthoquinonediazide, for example, JP-A-2004-4669, The crosslinking agent, acid generator, and itself are insoluble or hardly soluble in an aqueous alkali solution, but have a protecting group that can be cleaved by the action of an acid, and are soluble in an aqueous alkali solution after the protecting group is cleaved. There has been proposed a positive chemical amplification material characterized by containing a resin. In addition, JP 2004-264623 A, JP 2008-304902 A, and the like include an acetal structure and / or a ketal structure, a resin containing an epoxy group, and an acid generator. Radiation compositions have been proposed.
しかしながら、これらの感放射線性樹脂組成物を用いる場合にあっては、ポジ型化学増幅材料に特有に見られる露光後の引き置きによる問題、すなわち、化学増幅系材料から形成された膜を露光後引き置いた場合に、露光時に発生した酸が膜表面において雰囲気中の塩基性物質に中和されることによる失活や、酸の未露光部への拡散が起こり、所望のパターンが得られず、基板との密着性が低下するという問題があった(特開平6−66100号公報参照)。 However, in the case of using these radiation-sensitive resin compositions, there is a problem due to post-exposure leaving that is peculiar to positive-type chemically amplified materials, that is, after exposure of a film formed from a chemically amplified material. When left behind, the acid generated during exposure is deactivated by neutralizing the basic substance in the atmosphere on the film surface, and the acid diffuses into the unexposed area, and the desired pattern cannot be obtained. There has been a problem that the adhesion to the substrate is lowered (see JP-A-6-66100).
露光後の引き置きは、液晶パネル製造等における大型サイズのガラス基板を用いる場合には、製造プロセスで頻繁に発生するため、露光後の引き置きによる影響を受けることなく、安定的にパターン形成が可能な感放射線性樹脂組成物材料が求められている。 When a large-sized glass substrate is used in liquid crystal panel manufacturing, etc., the exposure after exposure frequently occurs in the manufacturing process, so that the pattern can be stably formed without being affected by the alignment after exposure. There is a need for possible radiation-sensitive resin composition materials.
本発明は、以上のような事情に基づいてなされたものであり、その目的は、感度等の一般的特性を十分満足し、かつ露光後の引き置きによるパターン形状不良、密着性不良の低減を可能とする感放射線性樹脂組成物を提供し、この感放射線性樹脂組成物から形成される硬化膜及びその形成方法、並びに当該硬化膜を備える表示素子を提供することを目的とする。 The present invention has been made based on the circumstances as described above, and its purpose is to sufficiently satisfy general characteristics such as sensitivity and to reduce pattern shape defects and adhesion defects by leaving after exposure. An object of the present invention is to provide a radiation-sensitive resin composition that can be made, and to provide a cured film formed from the radiation-sensitive resin composition, a method for forming the cured film, and a display element including the cured film.
上記課題を解決するためになされた発明は、
[A]同一又は異なる重合体中に、酸解離性基を含む構造単位(I)と架橋性基を含む構造単位(II)を含む重合成分、並びに
[B]光酸発生剤
[C]下記式(1)で示される化合物を含有する感放射線性樹脂組成物によって達成される。
The invention made to solve the above problems is
[A] Polymer component containing structural unit (I) containing an acid dissociable group and structural unit (II) containing a crosslinkable group in the same or different polymers, and [B] photoacid generator [C] It is achieved by a radiation sensitive resin composition containing a compound represented by the formula (1).
(式(1)において、Xは酸素原子または硫黄原子を示し、R1、R2はそれぞれ独立に、単結合または2から4価の有機基を示し、R3、R4はそれぞれ独立に、不飽和複素環基、炭素数11〜20のアルキル基、オキシラニル基、オキセタニル基、ビニル基、(メタ)アクリロイルオキシ基、水酸基、カルボキシル基、アルコキシシリル基、メルカプト基、スルホ基を示す。n,mはそれぞれ独立に1から3の整数を示す。)
また、上記課題を解決するためになされた別の発明は、当該感放射線性樹脂組成物から形成される硬化膜、及び当該硬化膜を備える表示素子
を含む。
(In Formula (1), X represents an oxygen atom or a sulfur atom, R 1 and R 2 each independently represents a single bond or a divalent to tetravalent organic group, and R 3 and R 4 each independently represent An unsaturated heterocyclic group, an alkyl group having 11 to 20 carbon atoms, an oxiranyl group, an oxetanyl group, a vinyl group, a (meth) acryloyloxy group, a hydroxyl group, a carboxyl group, an alkoxysilyl group, a mercapto group, and a sulfo group. m represents an integer of 1 to 3 independently.)
Moreover, another invention made | formed in order to solve the said subject contains the display element provided with the cured film formed from the said radiation sensitive resin composition, and the said cured film.
さらに、上記課題を解決するためになされた別の発明は、
(1)当該感放射線性樹脂組成物を用い、基板上に塗膜を形成する工程、
(2)上記塗膜の少なくとも一部に放射線を照射する工程、
(3)上記放射線が照射された塗膜を現像する工程、及び
(4)上記現像された塗膜を加熱する工程
を有する硬化膜の形成方法である。
Furthermore, another invention made to solve the above problems is
(1) The process of forming a coating film on a board | substrate using the said radiation sensitive resin composition,
(2) A step of irradiating at least a part of the coating film with radiation,
(3) A method for forming a cured film, comprising: a step of developing the coating film irradiated with the radiation; and (4) a step of heating the developed coating film.
なお、「架橋性基」とは、同一又は異なる分子間に共有結合を形成することができる基をいう。 The “crosslinkable group” refers to a group that can form a covalent bond between the same or different molecules.
本発明は、感度等の一般的特性を十分満足し、かつ露光後の引き置きによるパターン形状不良、密着性不良の低減を可能とし、この感放射線性樹脂組成物から形成される硬化膜及びその形成方法、並びに当該硬化膜を備える表示素子を提供することができる。そのため当該感放射線性樹脂組成物、当該硬化膜及びその形成方法、並びに当該表示素子は、液晶表示デバイス等の製造プロセスに好適に使用することができる。 The present invention sufficiently satisfies general characteristics such as sensitivity, and enables reduction of pattern shape defects and adhesion defects by leaving after exposure, and a cured film formed from this radiation-sensitive resin composition and its A formation method and a display element including the cured film can be provided. Therefore, the said radiation sensitive resin composition, the said cured film, its formation method, and the said display element can be used suitably for manufacturing processes, such as a liquid crystal display device.
<感放射線性樹脂組成物>
本発明の感放射線性樹脂組成物は、[A]重合体成分、[B]光酸発生剤、[C]式(1)で示される化合物を含有する。また、当該感放射線性樹脂組成物は、好適成分として[D]環状エーテル基を有し[A]重合体成分が有する重合体とは異なる化合物(以下、「[D]化合物」ともいう)、[E]酸化防止剤を含有してもよい。さらに、当該感放射線性樹脂組成物は、本発明の効果を損なわない範囲で、その他の任意成分を含有してもよい。以下、各成分について詳述する。
<Radiation sensitive resin composition>
The radiation sensitive resin composition of the present invention contains [A] a polymer component, [B] a photoacid generator, and [C] a compound represented by the formula (1). In addition, the radiation-sensitive resin composition is a compound having a [D] cyclic ether group as a suitable component and different from the polymer that the [A] polymer component has (hereinafter also referred to as “[D] compound”), [E] You may contain antioxidant. Furthermore, the said radiation sensitive resin composition may contain another arbitrary component in the range which does not impair the effect of this invention. Hereinafter, each component will be described in detail.
<[A]重合体成分>
[A]同一又は異なる重合体中に、酸解離性基を含む構造単位(I)と架橋性基を含む構造単位(II)を含む重合成分である。[A]重合体成分が上記構造単位を有するため、当該感放射線性樹脂組成物は、感度に優れると共に、現像工程後やポストベーク工程後における未露光部の膜厚変化を抑制することができる。また、[A]重合体成分は、本発明の効果を損なわない範囲で、その他の構造単位を有していてもよい。なお、[A]重合体成分は、各構造単位を2種以上有していてもよい。
<[A] Polymer component>
[A] A polymerization component containing the structural unit (I) containing an acid dissociable group and the structural unit (II) containing a crosslinkable group in the same or different polymers. [A] Since the polymer component has the above structural unit, the radiation-sensitive resin composition is excellent in sensitivity and can suppress a change in the film thickness of the unexposed portion after the development process or after the post-baking process. . Moreover, the [A] polymer component may have another structural unit in the range which does not impair the effect of this invention. In addition, the [A] polymer component may have 2 or more types of each structural unit.
[A]重合体成分の態様としては、例えば、
(i)同一の重合体分子中に、構造単位(I)及び構造単位(II)を有する態様;
(ii)同一の重合体分子中に、構造単位(I)を有し、それとは異なる重合体分子中に構造単位(II)を有する態様等が挙げられる。
以下、各構造単位について詳述する。
[構造単位(I)]
構造単位(I)は、酸解離性基を有する構造単位であり、[A]重合体成分が構造単位(I)を有することで、当該感放射線性樹脂組成物の高感度化を達成し、得られるコンタクトホール等のパターン形状安定性を向上することが可能となる。酸解離性基は、カルボキシル基やフェノール性水酸基等を保護する保護基であり、酸解離性基を有する重合体はアルカリ水溶液に不溶又は難溶であるが、酸の作用により保護基が解裂し、該保護基が解裂した後は重合体をアルカリ水溶液に可溶性とすることができる基である。
酸解離性基を含む構造単位(I)としては、下記式(3)で表される構造単位及び下記式(4)で表される構造単位が好ましく、構造単位(I)としては、式(3)で表される構造単位及び式(4)で表される構造単位から選ばれる少なくとも一方できる。
[A] As an aspect of the polymer component, for example,
(I) an embodiment having the structural unit (I) and the structural unit (II) in the same polymer molecule;
(Ii) An embodiment in which the structural unit (I) is contained in the same polymer molecule and the structural unit (II) is contained in a different polymer molecule.
Hereinafter, each structural unit will be described in detail.
[Structural unit (I)]
The structural unit (I) is a structural unit having an acid dissociable group, and the [A] polymer component has the structural unit (I), thereby achieving high sensitivity of the radiation-sensitive resin composition, It is possible to improve the stability of the pattern shape of the obtained contact hole or the like. An acid dissociable group is a protecting group that protects a carboxyl group, a phenolic hydroxyl group, etc., and a polymer having an acid dissociable group is insoluble or hardly soluble in an alkaline aqueous solution, but the protecting group is cleaved by the action of an acid. In addition, after the protective group is cleaved, the polymer can be made soluble in an alkaline aqueous solution.
As the structural unit (I) containing an acid dissociable group, a structural unit represented by the following formula (3) and a structural unit represented by the following formula (4) are preferable. It can be at least one selected from the structural unit represented by 3) and the structural unit represented by formula (4).
式(3)中、R7は、水素原子又はメチル基を示す。R8は、炭素数1〜12のアルキル基であり、R9は、炭素数1〜12のアルキル基又は炭素数4〜20の1価の脂環式炭化水素基を示す。 In formula (3), R 7 represents a hydrogen atom or a methyl group. R 8 is an alkyl group having 1 to 12 carbon atoms, and R 9 represents an alkyl group having 1 to 12 carbon atoms or a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms.
上記R8及びR9で表される炭素数1〜12のアルキル基としては、例えば、メチル基、エチル基、n−プロピル基、n−ブチル基、n−ペンチル基、n−ヘキシル基、n−オクチル基等の直鎖状アルキル基;i−プロピル基、i−ブチル基、t−ブチル基、ネオペンチル基等の分岐状のアルキル基等が挙げられる。 Examples of the alkyl group having 1 to 12 carbon atoms represented by R 8 and R 9 include, for example, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n -Linear alkyl groups such as octyl group; branched alkyl groups such as i-propyl group, i-butyl group, t-butyl group and neopentyl group.
上記R9で表される炭素数4〜20の1価の脂環式炭化水素基としては、例えば、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロデシル基、メチルシクロヘキシル基、エチルシクロヘキシル基等の単環式シクロアルキル基;シクロブテニル基、シクロペンテニル基、シクロヘキセニル基、シクロヘプテニル基、シクロオクテニル基、シクロデセニル基、シクロペンタジエニル基、シクロヘキサジエニル基、シクロオクタジエニル基、シクロデカジエン等の単環式シクロアルケニル基;ビシクロ[2.2.1]ヘプチル基、ビシクロ[2.2.2]オクチル基、トリシクロ[5.2.1.02,6]デシル基、トリシクロ[3.3.1.13,7]デシル基、テトラシクロ[6.2.1.13,6.02,7]ドデシル基、ノルボルニル基、アダマンチル基等の多環式シクロアルキル基等が挙げられる。 Examples of the monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms represented by R 9 include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, and a methylcyclohexyl group. Monocyclic cycloalkyl groups such as ethylcyclohexyl group; cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, cyclooctenyl group, cyclodecenyl group, cyclopentadienyl group, cyclohexadienyl group, cyclooctadienyl group, Monocyclic cycloalkenyl group such as cyclodecadiene; bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, tricyclo [5.2.1.0 2,6 ] decyl group, tricyclo [3.3.1.1 3,7] decyl group, tetracyclo [6.2 1.1 3,6. 0 2,7 ] dodecyl group, norbornyl group, acyclic cycloalkyl group such as adamantyl group and the like.
構造単位(I)の式(3)で示される化合物としては、例えば、下記式(3−1)〜(3−10)で表される構造単位等が挙げられる。 Examples of the compound represented by the formula (3) of the structural unit (I) include structural units represented by the following formulas (3-1) to (3-10).
上記式(3−1)〜(3−10)中、R7は、上記式(3)と同義である。 In the above formulas (3-1) to (3-10), R 7 has the same meaning as the above formula (3).
構造単位(I)の式(3)で表される構造単位を与える単量体としては、例えば、メタクリル酸1−エトキシエチル、メタクリル酸1−ブトキシエチル、メタクリル酸1−(トリシクロデカニルオキシ)エチル、メタクリル酸1−(ペンタシクロペンタデカニルメチルオキシ)エチル、メタクリル酸1−(ペンタシクロペンタデカニルオキシ)エチル、メタクリル酸1−(テトラシクロドデカニルメチルオキシ)エチル、メタクリル酸1−(アダマンチルオキシ)エチル等が挙げられる。 Examples of the monomer that gives the structural unit represented by the formula (3) of the structural unit (I) include 1-ethoxyethyl methacrylate, 1-butoxyethyl methacrylate, 1- (tricyclodecanyloxy methacrylate). ) Ethyl, 1- (pentacyclopentadecanylmethyloxy) ethyl methacrylate, 1- (pentacyclopentadecanyloxy) ethyl methacrylate, 1- (tetracyclododecanylmethyloxy) ethyl methacrylate, 1-methacrylic acid 1- And (adamantyloxy) ethyl.
式(4)中、R10は、水素原子又はメチル基を示す。R11からR17の炭素数1〜12のアルキル基としては、例えば、メチル基、エチル基、n−プロピル基、n−ブチル基等の直鎖状のアルキル基;i−プロピル基、i−ブチル基、sec−ブチル基、t−ブチル基等の分岐状のアルキル基;エテニル基、n−プロペニル基等の直鎖状のアルケニル基;i−プロペニル基、i−ブテニル基等の分岐状のアルケニル基等が挙げられる。 In formula (4), R 10 represents a hydrogen atom or a methyl group. Examples of the alkyl group having 1 to 12 carbon atoms of R 11 to R 17 include a linear alkyl group such as a methyl group, an ethyl group, an n-propyl group, and an n-butyl group; an i-propyl group, i- Branched alkyl groups such as butyl group, sec-butyl group and t-butyl group; linear alkenyl groups such as ethenyl group and n-propenyl group; branched chains such as i-propenyl group and i-butenyl group An alkenyl group etc. are mentioned.
構造単位(I)の式(4)で示される化合物としては、例えば、下記式(4−1)〜(4−5)で表される構造単位等が挙げられる。 Examples of the compound represented by the formula (4) of the structural unit (I) include structural units represented by the following formulas (4-1) to (4-5).
上記式(4−1)〜(4−5)中、R10は、上記式(4)と同義である。 In the above formulas (4-1) to (4-5), R 10 has the same meaning as the above formula (4).
構造単位(I)の式(4)で表される構造単位を与える単量体としては、テトラヒドロ−2H−ピラン−2−イルメタクリレートが好ましい。 As the monomer that gives the structural unit represented by the formula (4) of the structural unit (I), tetrahydro-2H-pyran-2-yl methacrylate is preferable.
構造単位(I)の含有割合としては、[A]重合体成分を構成する全構造単位に対して、0.1モル%以上80モル%以下が好ましく、1モル%以上60モル%以下がより好ましい。
[構造単位(II)]
構造単位(II)は、架橋性基を含んでいる。[A]重合体成分が架橋性基を含む構造単位(II)を有することで、当該感放射線性樹脂組成物は、[A]重合体成分を構成する重合体同士又は[A]重合体成分を構成する重合体と後述する[D]化合物との架橋により、形成される硬化膜の強度を高めることができる。
The content of the structural unit (I) is preferably 0.1 mol% or more and 80 mol% or less, more preferably 1 mol% or more and 60 mol% or less with respect to all the structural units constituting the [A] polymer component. preferable.
[Structural unit (II)]
The structural unit (II) contains a crosslinkable group. [A] When the polymer component has the structural unit (II) containing a crosslinkable group, the radiation-sensitive resin composition can be obtained by combining the polymers constituting the [A] polymer component or the [A] polymer component. The strength of the formed cured film can be increased by cross-linking the polymer constituting the compound [D] described later.
上記架橋性基としては、例えば、重合性炭素−炭素二重結合を含む基、重合性炭素−炭素三重結合を含む基、オキシラニル基(1,2−エポキシ構造)、オキセタニル基(1,3−エポキシ構造)、アルコキシメチル基、ホルミル基、アセチル基、ジアルキルアミノメチル基、ジメチロールアミノメチル基等が挙げられる。 Examples of the crosslinkable group include a group containing a polymerizable carbon-carbon double bond, a group containing a polymerizable carbon-carbon triple bond, an oxiranyl group (1,2-epoxy structure), an oxetanyl group (1,3- Epoxy structure), alkoxymethyl group, formyl group, acetyl group, dialkylaminomethyl group, dimethylolaminomethyl group and the like.
上記架橋性基としては、(メタ)アクリロイル基、オキシラニル基及びオキセタニル基からなる群より選択される少なくとも1種であることが好ましい。これにより、形成される硬化膜の強度をより高めることができる。 The crosslinkable group is preferably at least one selected from the group consisting of a (meth) acryloyl group, an oxiranyl group, and an oxetanyl group. Thereby, the intensity | strength of the cured film formed can be raised more.
構造単位(II)としては、例えば、下記式で表される構造単位等が挙げられる。 Examples of the structural unit (II) include a structural unit represented by the following formula.
上記式中、Rは、水素原子又はメチル基である。 In the above formula, R is a hydrogen atom or a methyl group.
構造単位(II)を与える単量体としては、(メタ)アクリロイル基、オキシラニル基、オキセタニル基を含む単量体が好ましく、オキシラニル基、オキセタニル基を含む単量体がより好ましく、メタクリル酸グリシジル、3−メタクリロイルオキシメチル−3−エチルオキセタン、3,4−エポキシシクロヘキシルメチルメタアクリレートが好ましい。 As the monomer that gives the structural unit (II), a monomer containing a (meth) acryloyl group, an oxiranyl group or an oxetanyl group is preferred, a monomer containing an oxiranyl group or an oxetanyl group is more preferred, glycidyl methacrylate, 3-Methacryloyloxymethyl-3-ethyloxetane and 3,4-epoxycyclohexylmethyl methacrylate are preferred.
構造単位(II)の含有割合としては、[A]重合体成分を構成する全構造単位に対して、0.1モル%以上80モル%以下が好ましく、1モル%以上60モル%以下がより好ましい。構造単位(II)の含有割合を上記範囲とすることで、形成される硬化膜の強度を効果的に高めることができる。
[その他の構造単位]
[A]重合体成分は、本発明の効果を損なわない範囲で、構造単位(I)、構造単位(II)以外のその他の構造単位を有していてもよい。
その他の構造単位を与える単量体としては、例えば、不飽和モノカルボン酸、水酸基を有する(メタ)アクリル酸エステル、(メタ)アクリル酸鎖状アルキルエステル、(メタ)アクリル酸環状アルキルエステル、(メタ)アクリル酸アリールエステル、不飽和芳香族化合物、共役ジエン、テトラヒドロフラン骨格等をもつ不飽和化合物が挙げられる。
不飽和モノカルボン酸としては、例えば、アクリル酸、メタクリル酸、クロトン酸等が挙げられる。不飽和ジカルボン酸としては、例えば、マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸等が挙げられる。不飽和ジカルボン酸の無水物としては、例えば、上記ジカルボン酸として例示した化合物の無水物等が挙げられる。多価カルボン酸のモノ[(メタ)アクリロイルオキシアルキル]エステルとしては、例えば、コハク酸モノ〔2−(メタ)アクリロイルオキシエチル〕、フタル酸モノ〔2−(メタ)アクリロイルオキシエチル〕、へキサヒドロフタル酸モノ2−(メタクリロイルオキシ)エチル等が挙げられる。両末端にカルボキシル基と水酸基とを有するポリマーのモノ(メタ)アクリレートとしては、例えば、ω−カルボキシポリカプロラクトンモノ(メタ)アクリレート等が挙げられる。カルボキシル基を有する不飽和多環式化合物及びその無水物としては、例えば、5−カルボキシビシクロ[2.2.1]ヘプト−2−エン、5,6−ジカルボキシビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−5−メチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−5−エチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−6−メチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−6−エチルビシクロ[2.2.1]ヘプト−2−エン、5,6−ジカルボキシビシクロ[2.2.1]ヘプト−2−エン無水物等が挙げられる。
The content ratio of the structural unit (II) is preferably 0.1 mol% or more and 80 mol% or less, more preferably 1 mol% or more and 60 mol% or less with respect to all the structural units constituting the polymer component [A]. preferable. By making the content rate of structural unit (II) into the said range, the intensity | strength of the cured film formed can be raised effectively.
[Other structural units]
[A] The polymer component may have other structural units other than the structural unit (I) and the structural unit (II) as long as the effects of the present invention are not impaired.
Examples of monomers that give other structural units include unsaturated monocarboxylic acids, (meth) acrylic acid esters having a hydroxyl group, (meth) acrylic acid chain alkyl esters, (meth) acrylic acid cyclic alkyl esters, ( Examples include unsaturated compounds having a meth) acrylic acid aryl ester, an unsaturated aromatic compound, a conjugated diene, a tetrahydrofuran skeleton and the like.
Examples of the unsaturated monocarboxylic acid include acrylic acid, methacrylic acid, and crotonic acid. Examples of the unsaturated dicarboxylic acid include maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid and the like. As an anhydride of unsaturated dicarboxylic acid, the anhydride of the compound illustrated as said dicarboxylic acid etc. are mentioned, for example. Examples of mono [(meth) acryloyloxyalkyl] esters of polyvalent carboxylic acids include, for example, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], hexane. And mono- (methacryloyloxy) ethyl hydrophthalate. Examples of the mono (meth) acrylate of a polymer having a carboxyl group and a hydroxyl group at both ends include ω-carboxypolycaprolactone mono (meth) acrylate. Examples of unsaturated polycyclic compounds having a carboxyl group and anhydrides thereof include 5-carboxybicyclo [2.2.1] hept-2-ene and 5,6-dicarboxybicyclo [2.2.1]. Hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5- Carboxy-6-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2. 2.1] hept-2-ene anhydride and the like.
これらのうち、モノカルボン酸、ジカルボン酸の無水物が好ましく、(メタ)アクリル酸、無水マレイン酸が、共重合反応性、アルカリ水溶液に対する溶解性及び入手の容易性からより好ましい。 Of these, monocarboxylic acid and dicarboxylic acid anhydrides are preferred, and (meth) acrylic acid and maleic anhydride are more preferred from the viewpoints of copolymerization reactivity, solubility in alkaline aqueous solutions, and availability.
水酸基を有する(メタ)アクリル酸エステルとしては、例えば、アクリル酸2−ヒドロキシエチル、アクリル酸3−ヒドロキシプロピル、アクリル酸4−ヒドロキシブチル、アクリル酸5−ヒドロキシペンチル、アクリル酸6−ヒドロキシヘキシル、メタククリル酸2−ヒドロキシエチル、メタククリル酸3−ヒドロキシプロピル、メタククリル酸4−ヒドロキシブチル、メタククリル酸5−ヒドロキシペンチル、メタククリル酸6−ヒドロキシヘキシル等が挙げられる。 Examples of the (meth) acrylic acid ester having a hydroxyl group include 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 5-hydroxypentyl acrylate, 6-hydroxyhexyl acrylate, and methacrylate. Examples include 2-hydroxyethyl acid, 3-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, 5-hydroxypentyl methacrylate, 6-hydroxyhexyl methacrylate, and the like.
(メタ)アクリル酸鎖状アルキルエステルとしては、例えば、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸n−ブチル、メタクリル酸sec−ブチル、メタクリル酸t−ブチル、メタクリル酸2−エチルヘキシル、メタクリル酸イソデシル、メタクリル酸n−ラウリル、メタクリル酸トリデシル、メタクリル酸n−ステアリル、アクリル酸メチル、アクリル酸エチル、アクリル酸n−ブチル、アクリル酸sec−ブチル、アクリル酸t−ブチル、アクリル酸2−エチルヘキシル、アクリル酸イソデシル、アクリル酸n−ラウリル、アクリル酸トリデシル、アクリル酸n−ステアリル等が挙げられる。 Examples of the (meth) acrylic acid chain alkyl ester include methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, t-butyl methacrylate, 2-ethylhexyl methacrylate, isodecyl methacrylate, N-lauryl methacrylate, tridecyl methacrylate, n-stearyl methacrylate, methyl acrylate, ethyl acrylate, n-butyl acrylate, sec-butyl acrylate, t-butyl acrylate, 2-ethylhexyl acrylate, acrylic acid Examples include isodecyl, n-lauryl acrylate, tridecyl acrylate, and n-stearyl acrylate.
(メタ)アクリル酸環状アルキルエステルとしては、例えば、メタクリル酸シクロヘキシル、メタクリル酸2−メチルシクロヘキシル、メタクリル酸トリシクロ[5.2.1.02,6]デカン−8−イル、メタクリル酸トリシクロ[5.2.1.02,6]デカン−8−イルオキシエチル、メタクリル酸イソボロニル、シクロヘキシルアクリレート、2−メチルシクロヘキシルアクリレート、トリシクロ[5.2.1.02,6]デカン−8−イルアクリレート、トリシクロ[5.2.1.02,6]デカン−8−イルオキシエチルアクリレート、イソボロニルアクリレート等が挙げられる。 Examples of the (meth) acrylic acid cyclic alkyl ester include cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, tricyclo [5.2.1.02,6] decan-8-yl methacrylate, and tricyclomethacrylate [5. 2.1.02,6] decan-8-yloxyethyl, isobornyl methacrylate, cyclohexyl acrylate, 2-methylcyclohexyl acrylate, tricyclo [5.2.1.02,6] decan-8-yl acrylate, tricyclo [ 5.2.1.02,6] decan-8-yloxyethyl acrylate, isobornyl acrylate and the like.
(メタ)アクリル酸アリールエステルとしては、例えば、メタクリル酸フェニル、メタクリル酸ベンジル、アクリル酸フェニル、アクリル酸ベンジル等が挙げられる。 Examples of the (meth) acrylic acid aryl ester include phenyl methacrylate, benzyl methacrylate, phenyl acrylate, and benzyl acrylate.
不飽和芳香族化合物としては、例えば、スチレン、α−メチルスチレン、o−メチルスチレン、m−メチルスチレン、p−メチルスチレン、p−メトキシスチレン、N−フェニルマレイミド、N−シクロヘキシルマレイミド、N−トリルマレイミド、N−ナフチルマレイミド、N−エチルマレイミド、N−ヘキシルマレイミド、N−ベンジルマレイミド等が挙げられる。 Examples of the unsaturated aromatic compound include styrene, α-methylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, p-methoxystyrene, N-phenylmaleimide, N-cyclohexylmaleimide, and N-tolyl. Maleimide, N-naphthylmaleimide, N-ethylmaleimide, N-hexylmaleimide, N-benzylmaleimide and the like can be mentioned.
共役ジエンとしては、例えば1,3−ブタジエン、イソプレン、2,3−ジメチル−1,3−ブタジエン等が挙げられる。 Examples of the conjugated diene include 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene and the like.
テトラヒドロフラン骨格を含有する不飽和化合物としては、例えば、テトラヒドロフルフリル(メタ)アクリレート、2−メタクリロイルオキシ−プロピオン酸テトラヒドロフルフリルエステル、3−(メタ)アクリロイルオキシテトラヒドロフラン−2−オン等が挙げられる。 Examples of the unsaturated compound containing a tetrahydrofuran skeleton include tetrahydrofurfuryl (meth) acrylate, 2-methacryloyloxy-propionic acid tetrahydrofurfuryl ester, 3- (meth) acryloyloxytetrahydrofuran-2-one, and the like.
その他の構造単位の含有割合としては、全構造単位に対して、好ましくは5モル%〜30モル%、より好ましくは10モル%〜25モル%である。その他の構造単位の含有割合を5モル%〜30モル%とすることで、アルカリ水溶液に対する溶解性を最適化すると共に放射線性感度に優れる感放射線性樹脂組成物が得られる。
<[A]重合体成分の合成方法>
[A]重合体成分は、例えば、所定の各構造単位に対応する単量体を、ラジカル重合開始剤を使用し、適当な溶媒中で重合することにより製造できる。例えば、単量体及びラジカル開始剤を含有する溶液を、反応溶媒又は単量体を含有する溶液に滴下して重合反応させる方法、単量体を含有する溶液と、ラジカル開始剤を含有する溶液とを各別に、反応溶媒又は単量体を含有する溶液に滴下して重合反応させる方法、各々の単量体を含有する複数種の溶液と、ラジカル開始剤を含有する溶液とを各別に、反応溶媒又は単量体を含有する溶液に滴下して重合反応させる方法等の方法で合成することが好ましい。
As a content rate of another structural unit, Preferably it is 5 mol%-30 mol% with respect to all the structural units, More preferably, it is 10 mol%-25 mol%. By setting the content of other structural units to 5 mol% to 30 mol%, a radiation sensitive resin composition that optimizes solubility in an aqueous alkali solution and is excellent in radiation sensitivity can be obtained.
<[A] Polymer component synthesis method>
[A] The polymer component can be produced, for example, by polymerizing a monomer corresponding to each predetermined structural unit in a suitable solvent using a radical polymerization initiator. For example, a method of dropping a solution containing a monomer and a radical initiator into a reaction solvent or a solution containing the monomer to cause a polymerization reaction, a solution containing the monomer, and a solution containing the radical initiator Separately, a method of dropping a reaction solvent or a monomer-containing solution into a polymerization reaction, a plurality of types of solutions containing each monomer, and a solution containing a radical initiator, It is preferable to synthesize by a method such as a method of dropping it into a reaction solvent or a solution containing a monomer to cause a polymerization reaction.
[A]重合体成分の重合反応に用いられる溶媒としては、例えば、後述する当該感放射線性樹脂組成物の調製の項において例示する溶媒等が挙げられる。 [A] Examples of the solvent used in the polymerization reaction of the polymer component include the solvents exemplified in the section of preparation of the radiation-sensitive resin composition described later.
重合反応に用いられる重合開始剤としては、一般的にラジカル重合開始剤として知られているものが使用できるが、例えば、2,2’−アゾビスイソブチロニトリル、2,2’−アゾビス(2,4−ジメチルバレロニトリル)、2,2’−アゾビス−(4−メトキシ−2,4−ジメチルバレロニトリル)、2,2’−アゾビス(2−メチルプロピオン酸メチル)等のアゾ化合物;ベンゾイルペルオキシド、ラウロイルペルオキシド、t−ブチルペルオキシピバレート、1,1’−ビス−(t−ブチルペルオキシ)シクロヘキサン等の有機過酸化物;過酸化水素等が挙げられる。 As the polymerization initiator used in the polymerization reaction, those generally known as radical polymerization initiators can be used. For example, 2,2′-azobisisobutyronitrile, 2,2′-azobis ( 2,4-Dimethylvaleronitrile), 2,2′-azobis- (4-methoxy-2,4-dimethylvaleronitrile), azo compounds such as 2,2′-azobis (methyl 2-methylpropionate); benzoyl Organic peroxides such as peroxide, lauroyl peroxide, t-butylperoxypivalate, 1,1′-bis- (t-butylperoxy) cyclohexane; hydrogen peroxide and the like.
[A]重合体成分の重合反応においては、分子量を調整するために分子量調整剤を使用することもできる。分子量調整剤としては、例えば、クロロホルム、四臭化炭素等のハロゲン化炭化水素類;n−ヘキシルメルカプタン、n−オクチルメルカプタン、n−ドデシルメルカプタン、t−ドデシルメルカプタン、チオグリコール酸等のメルカプタン類;ジメチルキサントゲンスルフィド、ジイソプロピルキサントゲンジスルフィド等のキサントゲン類;ターピノーレン、α−メチルスチレンダイマー等が挙げられる。 [A] In the polymerization reaction of the polymer component, a molecular weight modifier may be used to adjust the molecular weight. Examples of the molecular weight modifier include halogenated hydrocarbons such as chloroform and carbon tetrabromide; mercaptans such as n-hexyl mercaptan, n-octyl mercaptan, n-dodecyl mercaptan, t-dodecyl mercaptan, and thioglycolic acid; Examples thereof include xanthogens such as dimethylxanthogen sulfide and diisopropylxanthogen disulfide; terpinolene and α-methylstyrene dimer.
[A]重合体のゲルパーミエーションクロマトグラフィー(GPC)によるポリスチレン換算重量平均分子量(Mw)としては、2.0×103以上1.0×105以下が好ましく、5.0×103以上5.0×104以下がより好ましい。[A]重合体成分のMwを上記範囲とすることで当該感放射線性樹脂組成物の感度及びアルカリ現像性を高めることができる。 [A] The weight average molecular weight (Mw) in terms of polystyrene by gel permeation chromatography (GPC) of the polymer is preferably 2.0 × 10 3 or more and 1.0 × 10 5 or less, and preferably 5.0 × 10 3 or more. 5.0 × 10 4 or less is more preferable. [A] By making Mw of a polymer component into the said range, the sensitivity and alkali developability of the said radiation sensitive resin composition can be improved.
[A]重合体成分のGPCによるポリスチレン換算数平均分子量(Mn)としては、2.0×103以上1.0×105以下が好ましく、5.0×103以上5.0×104以下がより好ましい。[A]重合体のMnを上記範囲とすることで、当該感放射線性樹脂組成物の塗膜の硬化時の硬化反応性を向上させることができる。 [A] The number average molecular weight (Mn) in terms of polystyrene by GPC of the polymer component is preferably 2.0 × 10 3 or more and 1.0 × 10 5 or less, and 5.0 × 10 3 or more and 5.0 × 10 4. The following is more preferable. [A] By making Mn of a polymer into the said range, the cure reactivity at the time of hardening of the coating film of the said radiation sensitive resin composition can be improved.
[A]重合体成分の分子量分布(Mw/Mn)としては、3.0以下が好ましく、2.6以下がより好ましい。[A]重合体成分のMw/Mnを3.0以下とすることで、得られる硬化膜の現像性を高めることができる。
<[B]光酸発生剤>
[B]光酸発生剤は、放射線の照射によって酸を発生する化合物である。放射線としては、例えば、可視光線、紫外線、遠紫外線、電子線、X線等を使用できる。当該感放射線性樹脂組成物が[B]光酸発生剤を含有することで、当該感放射線性樹脂組成物は感放射線特性を発揮することができ、かつ良好な感度を有することができる。[B]光酸発生剤の当該感放射線性樹脂組成物における含有形態としては、後述するような化合物である光酸発生剤(以下、適宜「[B]光酸発生剤」ともいう)の形態でも、[A]重合体成分を構成する重合体の一部として組み込まれた光酸発生基の形態でも、これらの両方の形態でもよい。
[A] The molecular weight distribution (Mw / Mn) of the polymer component is preferably 3.0 or less, and more preferably 2.6 or less. [A] By making Mw / Mn of a polymer component 3.0 or less, the developability of the obtained cured film can be improved.
<[B] Photoacid generator>
[B] The photoacid generator is a compound that generates an acid upon irradiation with radiation. As the radiation, for example, visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray or the like can be used. When the radiation-sensitive resin composition contains a [B] photoacid generator, the radiation-sensitive resin composition can exhibit radiation-sensitive characteristics and have good sensitivity. [B] The form of inclusion of the photoacid generator in the radiation-sensitive resin composition is a form of a photoacid generator (hereinafter also referred to as “[B] photoacid generator” as appropriate) as a compound as described below. However, it may be in the form of a photoacid generating group incorporated as part of the polymer constituting the [A] polymer component, or in both forms.
[B]光酸発生剤としては、例えば、オキシムスルホネート化合物、オニウム塩、スルホンイミド化合物、ハロゲン含有化合物、ジアゾメタン化合物、スルホン化合物、スルホン酸エステル化合物、カルボン酸エステル化合物等が挙げられる。なお、これらの[B]光酸発生剤は、単独で又は2種類以上を組み合わせて用いてもよい。
[オキシムスルホネート化合物]
オキシムスルホネート化合物としては、下記式(5)で表されるオキシムスルホネート基を含む化合物が好ましい。
[B] Examples of the photoacid generator include oxime sulfonate compounds, onium salts, sulfonimide compounds, halogen-containing compounds, diazomethane compounds, sulfone compounds, sulfonic acid ester compounds, and carboxylic acid ester compounds. In addition, you may use these [B] photo-acid generators individually or in combination of 2 or more types.
[Oxime sulfonate compound]
As the oxime sulfonate compound, a compound containing an oxime sulfonate group represented by the following formula (5) is preferable.
上記式(1)中、R18は、炭素数1から12のアルキル基、炭素数1から12のフルオロアルキル基、炭素数4から12の脂環式炭化水素基、炭素数6から20のアリール基、又はこれらのアルキル基、脂環式炭化水素基及びアリール基が有する水素原子の一部又は全部が置換基で置換された基である。 In the above formula (1), R 18 is an alkyl group having 1 to 12 carbon atoms, a fluoroalkyl group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 4 to 12 carbon atoms, or an aryl having 6 to 20 carbon atoms. Or a group in which some or all of the hydrogen atoms of the alkyl group, alicyclic hydrocarbon group and aryl group are substituted with a substituent.
上記R18で表されるアルキル基としては、炭素数1〜12の直鎖状又は分岐状のアルキル基が好ましい。この炭素数1〜12の直鎖状又は分岐状のアルキル基は置換基により置換されていてもよく、上記置換基としては、例えば、炭素数1〜10のアルコキシ基、7,7−ジメチル−2−オキソノルボルニル基等の有橋式脂環基を含む脂環式基等が挙げられる。炭素数1から12のフルオロアルキル基としては、トリフルオロメチル基、ペンタフルオロエチル基、ヘプチルフルオロプロピル基等が挙げられる。 The alkyl group represented by R 18 is preferably a linear or branched alkyl group having 1 to 12 carbon atoms. The linear or branched alkyl group having 1 to 12 carbon atoms may be substituted with a substituent. Examples of the substituent include an alkoxy group having 1 to 10 carbon atoms and 7,7-dimethyl- Examples thereof include alicyclic groups containing a bridged alicyclic group such as a 2-oxonorbornyl group. Examples of the fluoroalkyl group having 1 to 12 carbon atoms include a trifluoromethyl group, a pentafluoroethyl group, and a heptylfluoropropyl group.
上記R1で表される脂環式炭化水素基としては、炭素数4〜12の脂環式炭化水素基が好ましい。この炭素数4〜12の脂環式炭化水素基は置換基により置換されていてもよく、上記置換基としては、例えば、炭素数1〜5のアルキル基、アルコキシ基、ハロゲン原子等が挙げられる。 The alicyclic hydrocarbon group represented by R 1 is preferably an alicyclic hydrocarbon group having 4 to 12 carbon atoms. The alicyclic hydrocarbon group having 4 to 12 carbon atoms may be substituted with a substituent, and examples of the substituent include an alkyl group having 1 to 5 carbon atoms, an alkoxy group, and a halogen atom. .
上記R18で表されるアリール基としては、炭素数6〜20のアリール基が好ましく、フェニル基、ナフチル基、トリル基、キシリル基がより好ましい。上記アリール基は置換基により置換されていてもよく、上記置換基としては、例えば、炭素数1〜5のアルキル基、アルコキシ基、ハロゲン原子等が挙げられる。 The aryl group represented by R 18 is preferably an aryl group having 6 to 20 carbon atoms, more preferably a phenyl group, a naphthyl group, a tolyl group, or a xylyl group. The aryl group may be substituted with a substituent, and examples of the substituent include an alkyl group having 1 to 5 carbon atoms, an alkoxy group, and a halogen atom.
上記式(5)で表されるオキシムスルホネート基を含有する化合物としては、例えば、下記式(5−1)、式(5−2)、式(5−3)で表されるオキシムスルホネート化合物等が挙げられる。 Examples of the compound containing an oxime sulfonate group represented by the formula (5) include oxime sulfonate compounds represented by the following formula (5-1), formula (5-2), and formula (5-3). Is mentioned.
上記式(5−1)、(5−2)中、式(5−3)中、R18は、上記式(5)と同義である。上記式(5−1)、(5−2)中R19は、炭素数1から12のアルキル基、炭素数1から12にフルオロアルキル基である。
式(5−3)中、Xは、アルキル基、アルコキシ基、又はハロゲン原子である。bは、0〜3の整数である。但し、Xが複数の場合、複数のXは同一であっても異なっていてもよい。
In the formulas (5-1) and (5-2), in the formula (5-3), R 18 has the same meaning as the formula (5). In the above formulas (5-1) and (5-2), R 19 is an alkyl group having 1 to 12 carbon atoms and a fluoroalkyl group having 1 to 12 carbon atoms.
In formula (5-3), X represents an alkyl group, an alkoxy group, or a halogen atom. b is an integer of 0-3. However, when there are a plurality of Xs, the plurality of Xs may be the same or different.
上記Xで表されるアルキル基としては、炭素数1〜4の直鎖状若しくは分岐状のアルキル基が好ましい。上記Xで表されるアルコキシ基としては、炭素数1〜4の直鎖状又は分岐状のアルコキシ基が好ましい。上記Xで表されるハロゲン原子としては、塩素原子、フッ素原子が好ましい
上記(5―3)で表されるオキシムスルホネート化合物としては、例えば、下記式(5−4)〜(5−8)で表される化合物等が挙げられる。
The alkyl group represented by X is preferably a linear or branched alkyl group having 1 to 4 carbon atoms. The alkoxy group represented by X is preferably a linear or branched alkoxy group having 1 to 4 carbon atoms. The halogen atom represented by X is preferably a chlorine atom or a fluorine atom. Examples of the oxime sulfonate compound represented by the above (5-3) include the following formulas (5-4) to (5-8). And the like.
上記式(5−4)〜(5−8)で表される化合物は、それぞれ(5−プロピルスルフォニルオキシイミノ−5H−チオフェン−2−イリデン)−(2−メチルフェニル)アセトニトリル、(5−オクチルスルフォニルオキシイミノ−5H−チオフェン−2−イリデン)−(2−メチルフェニル)アセトニトリル、(カンファースルフォニルオキシイミノ−5H−チオフェン−2−イリデン)−(2−メチルフェニル)アセトニトリル、(5−p−トルエンスルフォニルオキシイミノ−5H−チオフェン−2−イリデン)−(2−メチルフェニル)アセトニトリル、(5−オクチルスルフォニルオキシイミノ)−(4−メトキシフェニル)アセトニトリルであり、市販品として入手できる。
[オニウム塩]
オニウム塩としては、例えば、ジフェニルヨードニウム塩、トリフェニルスルホニウム塩、スルホニウム塩、ベンゾチアゾニウム塩、テトラヒドロチオフェニウム塩等が挙げられる。
The compounds represented by the above formulas (5-4) to (5-8) are respectively (5-propylsulfonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl) acetonitrile, (5-octyl). Sulfonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl) acetonitrile, (camphorsulfonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl) acetonitrile, (5-p-toluene) Sulphonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl) acetonitrile and (5-octylsulfonyloxyimino)-(4-methoxyphenyl) acetonitrile, which are commercially available.
[Onium salt]
Examples of the onium salt include diphenyliodonium salt, triphenylsulfonium salt, sulfonium salt, benzothiazonium salt, tetrahydrothiophenium salt, and the like.
上記ジフェニルヨードニウム塩としては、例えば、ジフェニルヨードニウムテトラフルオロボレート、ジフェニルヨードニウムヘキサフルオロホスホネート、ジフェニルヨードニウムヘキサフルオロアルセネート、ジフェニルヨードニウムトリフルオロメタンスルホナート、ジフェニルヨードニウムトリフルオロアセテート、ジフェニルヨードニウム−p−トルエンスルホナート、ジフェニルヨードニウムブチルトリス(2,6−ジフルオロフェニル)ボレート、4−メトキシフェニルフェニルヨードニウムテトラフルオロボレート、ビス(4−t−ブチルフェニル)ヨードニウムテトラフルオロボレート、ビス(4−t−ブチルフェニル)ヨードニウムヘキサフルオロアルセネート、ビス(4−t−ブチルフェニル)ヨードニウムトリフルオロメタンスルホナート、ビス(4−t−ブチルフェニル)ヨードニウムトリフルオロアセテート、ビス(4−t−ブチルフェニル)ヨードニウム−p−トルエンスルホナート、ビス(4−t−ブチルフェニル)ヨードニウムカンファースルホン酸等が挙げられる。 Examples of the diphenyliodonium salt include diphenyliodonium tetrafluoroborate, diphenyliodonium hexafluorophosphonate, diphenyliodonium hexafluoroarsenate, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium trifluoroacetate, diphenyliodonium-p-toluenesulfonate, Diphenyliodonium butyltris (2,6-difluorophenyl) borate, 4-methoxyphenylphenyliodonium tetrafluoroborate, bis (4-t-butylphenyl) iodonium tetrafluoroborate, bis (4-t-butylphenyl) iodonium hexafluoro Arsenate, bis (4-tert-butylphenyl) iodonium triflate Romethanesulfonate, bis (4-t-butylphenyl) iodonium trifluoroacetate, bis (4-t-butylphenyl) iodonium-p-toluenesulfonate, bis (4-t-butylphenyl) iodonium camphorsulfonic acid, etc. Can be mentioned.
上記トリフェニルスルホニウム塩としては、例えば、トリフェニルスルホニウムトリフルオロメタンスルホナート、トリフェニルスルホニウムカンファースルホン酸、トリフェニルスルホニウムテトラフルオロボレート、トリフェニルスルホニウムトリフルオロアセテート、トリフェニルスルホニウム−p−トルエンスルホナート、トリフェニルスルホニウムブチルトリス(2、6−ジフルオロフェニル)ボレート等が挙げられる。 Examples of the triphenylsulfonium salt include triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium camphorsulfonic acid, triphenylsulfonium tetrafluoroborate, triphenylsulfonium trifluoroacetate, triphenylsulfonium-p-toluenesulfonate, Examples thereof include phenylsulfonium butyl tris (2,6-difluorophenyl) borate.
上記スルホニウム塩としては、例えば、アルキルスルホニウム塩、ベンジルスルホニウム塩、ジベンジルスルホニウム塩、置換ベンジルスルホニウム塩等が挙げられる。 Examples of the sulfonium salt include alkylsulfonium salts, benzylsulfonium salts, dibenzylsulfonium salts, substituted benzylsulfonium salts, and the like.
上記アルキルスルホニウム塩としては、例えば、4−アセトキシフェニルジメチルスルホニウムヘキサフルオロアンチモネート、4−アセトキシフェニルジメチルスルホニウムヘキサフルオロアルセネート、ジメチル−4−(ベンジルオキシカルボニルオキシ)フェニルスルホニウムヘキサフルオロアンチモネート、ジメチル−4−(ベンゾイルオキシ)フェニルスルホニウムヘキサフルオロアンチモネート、ジメチル−4−(ベンゾイルオキシ)フェニルスルホニウムヘキサフルオロアルセネート、ジメチル−3−クロロ−4−アセトキシフェニルスルホニウムヘキサフルオロアンチモネート等が挙げられる。 Examples of the alkylsulfonium salt include 4-acetoxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium hexafluoroarsenate, dimethyl-4- (benzyloxycarbonyloxy) phenylsulfonium hexafluoroantimonate, dimethyl- Examples include 4- (benzoyloxy) phenylsulfonium hexafluoroantimonate, dimethyl-4- (benzoyloxy) phenylsulfonium hexafluoroarsenate, dimethyl-3-chloro-4-acetoxyphenylsulfonium hexafluoroantimonate, and the like.
上記ベンジルスルホニウム塩としては、例えば、ベンジル−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロアンチモネート、ベンジル−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロホスフェート、4−アセトキシフェニルベンジルメチルスルホニウムヘキサフルオロアンチモネート、ベンジル−4−メトキシフェニルメチルスルホニウムヘキサフルオロアンチモネート、ベンジル−2−メチル−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロアンチモネート、ベンジル−3−クロロ−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロアルセネート、4−メトキシベンジル−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロホスフェート等が挙げられる。 Examples of the benzylsulfonium salt include benzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, benzyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate, 4-acetoxyphenylbenzylmethylsulfonium hexafluoroantimonate, benzyl-4- Methoxyphenylmethylsulfonium hexafluoroantimonate, benzyl-2-methyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, benzyl-3-chloro-4-hydroxyphenylmethylsulfonium hexafluoroarsenate, 4-methoxybenzyl-4- Examples thereof include hydroxyphenylmethylsulfonium hexafluorophosphate.
上記ジベンジルスルホニウム塩としては、例えば、ジベンジル−4−ヒドロキシフェニルスルホニウムヘキサフルオロアンチモネート、ジベンジル−4−ヒドロキシフェニルスルホニウムヘキサフルオロホスフェート、4−アセトキシフェニルジベンジルスルホニウムヘキサフルオロアンチモネート、ジベンジル−4−メトキシフェニルスルホニウムヘキサフルオロアンチモネート、ジベンジル−3−クロロ−4−ヒドロキシフェニルスルホニウムヘキサフルオロアルセネート、ジベンジル−3−メチル−4−ヒドロキシ−5−t−ブチルフェニルスルホニウムヘキサフルオロアンチモネート、ベンジル−4−メトキシベンジル−4−ヒドロキシフェニルスルホニウムヘキサフルオロホスフェート等が挙げられる。 Examples of the dibenzylsulfonium salt include dibenzyl-4-hydroxyphenylsulfonium hexafluoroantimonate, dibenzyl-4-hydroxyphenylsulfonium hexafluorophosphate, 4-acetoxyphenyldibenzylsulfonium hexafluoroantimonate, and dibenzyl-4-methoxy. Phenylsulfonium hexafluoroantimonate, dibenzyl-3-chloro-4-hydroxyphenylsulfonium hexafluoroarsenate, dibenzyl-3-methyl-4-hydroxy-5-t-butylphenylsulfonium hexafluoroantimonate, benzyl-4-methoxy Examples include benzyl-4-hydroxyphenylsulfonium hexafluorophosphate.
上記置換ベンジルスルホニウム塩としては、例えば、p−クロロベンジル−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロアンチモネート、p−ニトロベンジル−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロアンチモネート、p−クロロベンジル−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロホスフェート、p−ニトロベンジル−3−メチル−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロアンチモネート、3,5−ジクロロベンジル−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロアンチモネート、o−クロロベンジル−3−クロロ−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロアンチモネート等が挙げられる。 Examples of the substituted benzylsulfonium salt include p-chlorobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, p-nitrobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, and p-chlorobenzyl-4-hydroxy. Phenylmethylsulfonium hexafluorophosphate, p-nitrobenzyl-3-methyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, 3,5-dichlorobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, o-chlorobenzyl- Examples include 3-chloro-4-hydroxyphenylmethylsulfonium hexafluoroantimonate.
上記ベンゾチアゾニウム塩としては、例えば、3−ベンジルベンゾチアゾニウムヘキサフルオロアンチモネート、3−ベンジルベンゾチアゾニウムヘキサフルオロホスフェート、3−ベンジルベンゾチアゾニウムテトラフルオロボレート、3−(p−メトキシベンジル)ベンゾチアゾニウムヘキサフルオロアンチモネート、3−ベンジル−2−メチルチオベンゾチアゾニウムヘキサフルオロアンチモネート、3−ベンジル−5−クロロベンゾチアゾニウムヘキサフルオロアンチモネート等が挙げられる。 Examples of the benzothiazonium salt include 3-benzylbenzothiazonium hexafluoroantimonate, 3-benzylbenzothiazonium hexafluorophosphate, 3-benzylbenzothiazonium tetrafluoroborate, 3- (p- Methoxybenzyl) benzothiazonium hexafluoroantimonate, 3-benzyl-2-methylthiobenzothiazonium hexafluoroantimonate, 3-benzyl-5-chlorobenzothiazonium hexafluoroantimonate and the like.
上記テトラヒドロチオフェニウム塩としては、例えば、4,7−ジ−n−ブトキシ−1−ナフチルテトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウムノナフルオロ−n−ブタンスルホネート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウム−1,1,2,2−テトラフルオロ−2−(ノルボルナン−2−イル)エタンスルホネート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウム−2−(5−t−ブトキシカルボニルオキシビシクロ[2.2.1]ヘプタン−2−イル)−1,1,2,2−テトラフルオロエタンスルホネート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウム−2−(6−t−ブトキシカルボニルオキシビシクロ[2.2.1]ヘプタン−2−イル)−1,1,2,2−テトラフルオロエタンスルホネート等が挙げられる。
[スルホンイミド化合物]
スルホンイミド化合物としては、例えば、N−(トリフルオロメチルスルホニルオキシ)スクシンイミド、N−(カンファスルホニルオキシ)スクシンイミド、N−(4−メチルフェニルスルホニルオキシ)スクシンイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)スクシンイミド、N−(4−フルオロフェニルスルホニルオキシ)スクシンイミド、N−(トリフルオロメチルスルホニルオキシ)フタルイミド、N−(カンファスルホニルオキシ)フタルイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)フタルイミド、N−(2−フルオロフェニルスルホニルオキシ)フタルイミド、N−(トリフルオロメチルスルホニルオキシ)ジフェニルマレイミド、N−(カンファスルホニルオキシ)ジフェニルマレイミド、4−メチルフェニルスルホニルオキシ)ジフェニルマレイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)ジフェニルマレイミド、N−(4−フルオロフェニルスルホニルオキシ)ジフェニルマレイミド、N−(4−フルオロフェニルスルホニルオキシ)ジフェニルマレイミド、N−(フェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(4−メチルフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(トリフルオロメタンスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(ノナフルオロブタンスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(カンファスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(カンファスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(トリフルオロメチルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(4−メチルフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(4−メチルフェニルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(4−フルオロフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(4−フルオロフェニルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(トリフルオロメチルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(カンファスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(4−メチルフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(4−フルオロフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(トリフルオロメチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(カンファスルホニルオキシ)ナフチルジカルボキシイミド、N−(4−メチルフェニルスルホニルオキシ)ナフチルジカルボキシイミド、N−(フェニルスルホニルオキシ)ナフチルジカルボキシイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)ナフチルジカルボキシイミド、N−(4−フルオロフェニルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ペンタフルオロエチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ヘプタフルオロプロピルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ノナフルオロブチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(エチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(プロピルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ブチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ペンチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ヘキシルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ヘプチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(オクチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ノニルスルホニルオキシ)ナフチルジカルボキシイミド等が挙げられる
[ハロゲン含有化合物]
ハロゲン含有化合物としては、例えば、ハロアルキル基含有炭化水素化合物、ハロアルキル基含有ヘテロ環状化合物等が挙げられる。
[ジアゾメタン化合物]
ジアゾメタン化合物としては、例えば、ビス(トリフルオロメチルスルホニル)ジアゾメタン、ビス(シクロヘキシルスルホニル)ジアゾメタン、ビス(フェニルスルホニル)ジアゾメタン、ビス(p−トリルスルホニル)ジアゾメタン、ビス(2,4−キシリルスルホニル)ジアゾメタン、ビス(p−クロロフェニルスルホニル)ジアゾメタン、メチルスルホニル−p−トルエンスルホニルジアゾメタン、シクロヘキシルスルホニル(1,1−ジメチルエチルスルホニル)ジアゾメタン、ビス(1,1−ジメチルエチルスルホニル)ジアゾメタン、フェニルスルホニル(ベンゾイル)ジアゾメタン等が挙げられる。
[スルホン化合物]
スルホン化合物としては、例えば、β−ケトスルホン化合物、β−スルホニルスルホン化合物、ジアリールジスルホン化合物等が挙げられる。
[スルホン酸エステル化合物]
スルホン酸エステル化合物としては、例えば、アルキルスルホン酸エステル、ハロアルキルスルホン酸エステル、アリールスルホン酸エステル、イミノスルホネート等が挙げられる。
[カルボン酸エステル化合物]
カルボン酸エステル化合物としては、例えば、カルボン酸o−ニトロベンジルエステル等が挙げられる。
Examples of the tetrahydrothiophenium salt include 4,7-di-n-butoxy-1-naphthyltetrahydrothiophenium trifluoromethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium. Trifluoromethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium nonafluoro-n-butanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium-1 , 1,2,2-Tetrafluoro-2- (norbornan-2-yl) ethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium-2- (5-t-butoxycarbonyl) Oxybicyclo [2.2.1] heptan-2-yl) -1 1,2,2-tetrafluoroethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium-2- (6-t-butoxycarbonyloxybicyclo [2.2.1] heptane- 2-yl) -1,1,2,2-tetrafluoroethanesulfonate and the like.
[Sulfonimide compound]
Examples of the sulfonimide compound include N- (trifluoromethylsulfonyloxy) succinimide, N- (camphorsulfonyloxy) succinimide, N- (4-methylphenylsulfonyloxy) succinimide, N- (2-trifluoromethylphenylsulfonyl). Oxy) succinimide, N- (4-fluorophenylsulfonyloxy) succinimide, N- (trifluoromethylsulfonyloxy) phthalimide, N- (camphorsulfonyloxy) phthalimide, N- (2-trifluoromethylphenylsulfonyloxy) phthalimide, N- (2-fluorophenylsulfonyloxy) phthalimide, N- (trifluoromethylsulfonyloxy) diphenylmaleimide, N- (camphorsulfonyloxy) diphenyl Reimide, 4-methylphenylsulfonyloxy) diphenylmaleimide, N- (2-trifluoromethylphenylsulfonyloxy) diphenylmaleimide, N- (4-fluorophenylsulfonyloxy) diphenylmaleimide, N- (4-fluorophenylsulfonyloxy) Diphenylmaleimide, N- (phenylsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (4-methylphenylsulfonyloxy) bicyclo [2.2.1] Hept-5-ene-2,3-dicarboximide, N- (trifluoromethanesulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (nonafluorobutane Sulfonyloxy) bicyclo [2.2.1] hept -5-ene-2,3-dicarboximide, N- (camphorsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (camphorsulfonyloxy)- 7-oxabicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (trifluoromethylsulfonyloxy) -7-oxabicyclo [2.2.1] hept-5 Ene-2,3-dicarboximide, N- (4-methylphenylsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (4-methylphenylsulfonyl) Oxy) -7-oxabicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (2-trifluoromethylphenylsulfonyloxy) bicycl [2.2.1] Hept-5-ene-2,3-dicarboximide, N- (2-trifluoromethylphenylsulfonyloxy) -7-oxabicyclo [2.2.1] hept-5 Ene-2,3-dicarboximide, N- (4-fluorophenylsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (4-fluorophenylsulfonyl) Oxy) -7-oxabicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (trifluoromethylsulfonyloxy) bicyclo [2.2.1] heptane-5,6 -Oxy-2,3-dicarboximide, N- (camphorsulfonyloxy) bicyclo [2.2.1] heptane-5,6-oxy-2,3-dicarboximide, N- (4 Methylphenylsulfonyloxy) bicyclo [2.2.1] heptane-5,6-oxy-2,3-dicarboximide, N- (2-trifluoromethylphenylsulfonyloxy) bicyclo [2.2.1] heptane -5,6-oxy-2,3-dicarboximide, N- (4-fluorophenylsulfonyloxy) bicyclo [2.2.1] heptane-5,6-oxy-2,3-dicarboximide, N -(Trifluoromethylsulfonyloxy) naphthyl dicarboximide, N- (camphorsulfonyloxy) naphthyl dicarboximide, N- (4-methylphenylsulfonyloxy) naphthyl dicarboximide, N- (phenylsulfonyloxy) naphthyl dicarboximide Imido, N- (2-trifluoromethylphenylsulfonyl) Xyl) naphthyl dicarboximide, N- (4-fluorophenylsulfonyloxy) naphthyl dicarboximide, N- (pentafluoroethylsulfonyloxy) naphthyl dicarboximide, N- (heptafluoropropylsulfonyloxy) naphthyl dicarboximide, N- (nonafluorobutylsulfonyloxy) naphthyl dicarboximide, N- (ethylsulfonyloxy) naphthyl dicarboximide, N- (propylsulfonyloxy) naphthyl dicarboximide, N- (butylsulfonyloxy) naphthyl dicarboximide, N- (pentylsulfonyloxy) naphthyl dicarboximide, N- (hexylsulfonyloxy) naphthyl dicarboximide, N- (heptylsulfonyloxy) naphthyl dicarbox And xylimide, N- (octylsulfonyloxy) naphthyldicarboximide, N- (nonylsulfonyloxy) naphthyldicarboximide, and the like [halogen-containing compound].
Examples of the halogen-containing compound include haloalkyl group-containing hydrocarbon compounds and haloalkyl group-containing heterocyclic compounds.
[Diazomethane compounds]
Examples of the diazomethane compound include bis (trifluoromethylsulfonyl) diazomethane, bis (cyclohexylsulfonyl) diazomethane, bis (phenylsulfonyl) diazomethane, bis (p-tolylsulfonyl) diazomethane, and bis (2,4-xylylsulfonyl) diazomethane. Bis (p-chlorophenylsulfonyl) diazomethane, methylsulfonyl-p-toluenesulfonyldiazomethane, cyclohexylsulfonyl (1,1-dimethylethylsulfonyl) diazomethane, bis (1,1-dimethylethylsulfonyl) diazomethane, phenylsulfonyl (benzoyl) diazomethane Etc.
[Sulfone compound]
Examples of the sulfone compound include β-ketosulfone compounds, β-sulfonylsulfone compounds, diaryl disulfone compounds, and the like.
[Sulfonic acid ester compounds]
Examples of the sulfonate compound include alkyl sulfonate, haloalkyl sulfonate, aryl sulfonate, and imino sulfonate.
[Carboxylic ester compounds]
Examples of the carboxylic acid ester compound include carboxylic acid o-nitrobenzyl ester.
[B]光酸発生剤としては、オキシムスルホネート化合物、オニウム塩、スルホン酸エステル化合物が好ましく、オキシムスルホネート化合物がより好ましい。上記オキシムスルホネート化合物としては、上記式(5)で表されるオキシムスルホネート基を含む化合物が好ましく、上記式(5−4)〜(5−8)で表される化合物がより好ましい。
また、上記オニウム塩としては、テトラヒドロチオフェニウム塩、ベンジルスルホニウム塩が好ましく、4,7−ジ−n−ブトキシ−1−ナフチルテトラヒドロチオフェニウムトリフルオロメタンスルホネート、ベンジル−4−ヒドロキシフェニルメチルスルホニウムヘキサフルオロホスフェートがより好ましく、4,7−ジ−n−ブトキシ−1−ナフチルテトラヒドロチオフェニウムトリフルオロメタンスルホネートがさらに好ましい。上記スルホン酸エステル化合物としては、ハロアルキルスルホン酸エステルが好ましく、N−ヒドロキシナフタルイミド−トリフルオロメタンスルホン酸エステルがより好ましい。[B]光酸発生剤を上記化合物とすることで、当該感放射線性樹脂組成物は、感度及び溶解性を向上させることができる。
[B] The photoacid generator is preferably an oxime sulfonate compound, an onium salt, or a sulfonate compound, and more preferably an oxime sulfonate compound. As said oxime sulfonate compound, the compound containing the oxime sulfonate group represented by said Formula (5) is preferable, and the compound represented by said Formula (5-4)-(5-8) is more preferable.
The onium salt is preferably a tetrahydrothiophenium salt or a benzylsulfonium salt, such as 4,7-di-n-butoxy-1-naphthyltetrahydrothiophenium trifluoromethanesulfonate, benzyl-4-hydroxyphenylmethylsulfonium hexa Fluorophosphate is more preferable, and 4,7-di-n-butoxy-1-naphthyltetrahydrothiophenium trifluoromethanesulfonate is more preferable. As the sulfonic acid ester compound, a haloalkylsulfonic acid ester is preferable, and N-hydroxynaphthalimide-trifluoromethanesulfonic acid ester is more preferable. [B] By making a photo-acid generator into the said compound, the said radiation sensitive resin composition can improve a sensitivity and solubility.
[B]光酸発生剤の含有量としては、[A]重合体成分100質量部に対して、0.1質量部〜10質量部が好ましく、1質量部〜5質量部がより好ましい。[B]光酸発生剤の含有量を上記範囲とすることで、当該感放射線性樹脂組成物の感度を最適化し、透明性を維持しつつ表面硬度が高い硬化膜を形成できる。
<[C]化合物>
本発明における[C]化合物は、下記式(1)で示される化合物である。[C]化合物は、ポジ型化学増幅材料に特有に見られる露光後の引き置きにより、露光時に発生した酸の未露光部への拡散によるパターン形状不良、基板との低密着性を低減する効果がある。
通常、化学増幅材料は、酸の過剰な拡散による弊害を防止するため、微量の塩基性化合物を含有する場合がある。塩基性化合物は酸の過剰な拡散防止に効果はあるが、塩基性化合物を多量に含むことで感度低下を引き起こす弊害が知られている。
本発明における[C]化合物は、式(1)の−NH−CO−NH−部位や−NH−CS−NH−部位を有する。これらの部位が弱い求核性を有することから、通常の塩基性化合物に比べれば、酸の拡散低減効果は低いが、多量に使用しても感度低下を誘発しない利点がある。
[B] As content of a photo-acid generator, 0.1 mass part-10 mass parts are preferable with respect to 100 mass parts of [A] polymer components, and 1 mass part-5 mass parts are more preferable. [B] By setting the content of the photoacid generator in the above range, the sensitivity of the radiation-sensitive resin composition can be optimized, and a cured film having high surface hardness can be formed while maintaining transparency.
<[C] Compound>
The [C] compound in the present invention is a compound represented by the following formula (1). The compound [C] has the effect of reducing pattern shape defects and low adhesion to the substrate due to diffusion of the acid generated during exposure to the unexposed area by the post-exposure leaving characteristic of positive chemical amplification materials. There is.
In general, a chemical amplification material may contain a trace amount of a basic compound in order to prevent harmful effects caused by excessive diffusion of acid. Although basic compounds are effective in preventing excessive diffusion of acids, there is a known problem that sensitivity is lowered by containing a large amount of basic compounds.
The [C] compound in the present invention has a -NH-CO-NH- site or a -NH-CS-NH- site of the formula (1). Since these sites have weak nucleophilicity, the effect of reducing the diffusion of acid is lower than that of ordinary basic compounds, but there is an advantage of not causing a decrease in sensitivity even when used in a large amount.
式(1)において、Xは酸素原子または硫黄原子を示し、R1、R2はそれぞれ独立に、単結合または2から4価の有機基を示し、R3、R4はそれぞれ独立に、不飽和複素環基、炭素数11〜20のアルキル基、オキシラニル基、オキセタニル基、ビニル基、(メタ)アクリロイルオキシ基、水酸基、カルボキシル基、アルコキシシリル基、メルカプト基、スルホ基を示す。n,mはそれぞれ独立に1から3の整数を示す。
R1、R2の好ましい例としては、単結合、メチレン基、エチレン基、プロピレン基、ブチレン基、へプチレン基、ヘキサメチレン基、フェニレン基、−(C2H4O)mC2H4−、−(C3H6O)mC2H4−(mは1〜5の整数を表す。)、下記式(6)、下記式(7)で表される基等を挙げることができる。
In the formula (1), X represents an oxygen atom or a sulfur atom, R 1 and R 2 each independently represent a single bond or a divalent to tetravalent organic group, and R 3 and R 4 each independently A saturated heterocyclic group, an alkyl group having 11 to 20 carbon atoms, an oxiranyl group, an oxetanyl group, a vinyl group, a (meth) acryloyloxy group, a hydroxyl group, a carboxyl group, an alkoxysilyl group, a mercapto group, and a sulfo group are shown. n and m each independently represent an integer of 1 to 3.
Preferred examples of R 1 and R 2 include a single bond, a methylene group, an ethylene group, a propylene group, a butylene group, a heptylene group, a hexamethylene group, a phenylene group, and — (C 2 H 4 O) mC 2 H 4 —. , — (C 3 H 6 O) mC 2 H 4 — (m represents an integer of 1 to 5), groups represented by the following formula (6), and the following formula (7).
式中、e、f、gおよびhは、互いに同一であっても異なっていてもよく、0〜12の整数を表す。
R3、R4はそれぞれ独立に、不飽和複素環基、炭素数11〜20のアルキル基、オキシラニル基、オキセタニル基、ビニル基、(メタ)アクリロイルオキシ基、水酸基、カルボキシル基、アルコキシシリル基、メルカプト基、スルホ基を示す。
不飽和複素環基は、アリール(Aryl)基(芳香族炭化水素基)とは、区別されるものであり、不飽和結合を有する複素環基を示す。具体的には、2−フリル基、フルフリル基、2−チエニル基、2−テニル基、2−テノイル基、2−ピロリル基、2−ピリジル基、2−キノイル基、カルバゾール基、イミダゾール基、ベンゾイミダゾール基、インドール基等を示す。n,mはそれぞれ独立に1から3の整数を示す。
[C]化合物の中で、特に下記式(2)で示されるような、両末端に重合性基を有する化合物が特に好ましい。このような化合物は上述した[C]化合物の効果に加え、重合性基がポストベーク時の加熱で、熱架橋することで、硬化膜の高度を一層高めることが可能となり、得られるパターンの耐熱性や熱に対する形状安定性を向上することが可能となる。
In formula, e, f, g, and h may mutually be same or different, and represent the integer of 0-12.
R 3 and R 4 are each independently an unsaturated heterocyclic group, an alkyl group having 11 to 20 carbon atoms, an oxiranyl group, an oxetanyl group, a vinyl group, a (meth) acryloyloxy group, a hydroxyl group, a carboxyl group, an alkoxysilyl group, A mercapto group and a sulfo group are shown.
An unsaturated heterocyclic group is distinguished from an aryl group (aromatic hydrocarbon group) and represents a heterocyclic group having an unsaturated bond. Specifically, 2-furyl group, furfuryl group, 2-thienyl group, 2-thenyl group, 2-thenoyl group, 2-pyrrolyl group, 2-pyridyl group, 2-quinoyl group, carbazole group, imidazole group, benzoic group An imidazole group, an indole group, etc. are shown. n and m each independently represent an integer of 1 to 3.
Among the [C] compounds, particularly preferred are compounds having a polymerizable group at both ends, as shown by the following formula (2). In addition to the effects of the compound [C] described above, such a compound can further increase the height of the cured film by thermally crosslinking the polymerizable group by heating during post-baking, and the resulting pattern has heat resistance. And shape stability against heat can be improved.
式(2)において、Xは酸素原子または硫黄原子を示し、R1、R2はそれぞれ独立に、単結合または2から4価の有機基を示し、R5、R6はそれぞれ独立に、水素原子、メチルを示す。n,mはそれぞれ独立に1から3の整数を示す。
R1、R2は式(1)と同義である。
In the formula (2), X represents an oxygen atom or a sulfur atom, R 1 and R 2 each independently represents a single bond or a divalent to tetravalent organic group, and R 5 and R 6 each independently represent hydrogen. Atom, methyl. n and m each independently represent an integer of 1 to 3.
R 1 and R 2 have the same meaning as in formula (1).
上記(2)で表される[C]化合物としては、例えば、下記式(2−1)〜(2−6)で表される化合物等が挙げられる。 Examples of the [C] compound represented by the above (2) include compounds represented by the following formulas (2-1) to (2-6).
重合性ウレア化合物の具体例としては、例えば、1,3−ビス(アクリロイルオキシエチル)ウレア、1,3−ビス(メタアクリロイルオキシエチル)ウレア、1,3−ビス(メタアクリロイルオキシブチル)ウレア、1,3−ビス(メタアクリロイルオキシ−2−エトキシエチル)ウレア、1,3−ビス(m−メタアクリロイルオキシフェニル)ウレア、1,3−ビス(1,1−ビス(アクリロイルオキシメチル)エチル)ウレア等を挙げることができる。 Specific examples of the polymerizable urea compound include 1,3-bis (acryloyloxyethyl) urea, 1,3-bis (methacryloyloxyethyl) urea, 1,3-bis (methacryloyloxybutyl) urea, 1,3-bis (methacryloyloxy-2-ethoxyethyl) urea, 1,3-bis (m-methacryloyloxyphenyl) urea, 1,3-bis (1,1-bis (acryloyloxymethyl) ethyl) Examples include urea.
重合性ウレア化合物は、単独でまたは2種以上を混合して使用することができる。 A polymerizable urea compound can be used individually or in mixture of 2 or more types.
重合性ウレア化合物は、例えば、(メタ)アクリロイルオキシ基を有する不飽和イソシアネート化合物を、適当な溶媒中、水と共に反応させることにより製造することができる。(メタ)アクリロイルオキシ基を有する不飽和イソシアネート化合物としては、重合体〔A1〕の製造に使用される不飽和イソシアネート化合物と同様の化合物を挙げることができる。また、重合性ウレア化合物の製造に用いられる溶媒としては、例えば、テトラヒドロフラン、N,N−ジメチルホルムアミド、酢酸エチル、塩化メチレン等を挙げることができる。また、重合性ウレア化合物を製造する際の水の使用量は、(メタ)アクリロイルオキシ基を有する不飽和イソシアネート化合物に対して、好ましくは50〜500モル%、さらに好ましくは50〜100モル%である。このようにして得られた重合性ウレア化合物は、メタノール、エタノール等を用いて再結晶等により精製することが好ましい。 The polymerizable urea compound can be produced, for example, by reacting an unsaturated isocyanate compound having a (meth) acryloyloxy group with water in an appropriate solvent. As an unsaturated isocyanate compound which has a (meth) acryloyloxy group, the compound similar to the unsaturated isocyanate compound used for manufacture of a polymer [A1] can be mentioned. Moreover, as a solvent used for manufacture of a polymerizable urea compound, tetrahydrofuran, N, N- dimethylformamide, ethyl acetate, a methylene chloride etc. can be mentioned, for example. The amount of water used in producing the polymerizable urea compound is preferably 50 to 500 mol%, more preferably 50 to 100 mol%, based on the unsaturated isocyanate compound having a (meth) acryloyloxy group. is there. The polymerizable urea compound thus obtained is preferably purified by recrystallization or the like using methanol, ethanol or the like.
本発明の感放射線性樹脂組成物において、[C]化合物の使用量は、〔A〕重合体成分100質量部に対して、好ましくは0.1〜100質量部、より好ましくは1〜50質量部、さらに好ましくは3〜20質量部である。[C]化合物の使用量が0.1重量部未満では、所望の効果が得られないおそれがあり、一方100質量部を超えると、得られる感放射線性樹脂組成物の保存中に析出物が発生するおそれがある。
<[D]環状エーテル基を有する化合物>
[D]化合物は、環状エーテル基を有し、かつ[A]重合体成分が有する重合体とは異なる化合物である。当該感放射線性樹脂組成物が[D]化合物を含有することで、[D]化合物の熱反応性により[A]重合体成分等の架橋を促進し、形成される硬化膜の硬度をより高めることができると共に、当該感放射線性樹脂組成物の感度を高めることができる。なお、[C]化合物は、単独で又は2種以上を組み合わせてもちいてもよい。
In the radiation sensitive resin composition of the present invention, the amount of the [C] compound to be used is preferably 0.1 to 100 parts by mass, more preferably 1 to 50 parts by mass with respect to 100 parts by mass of the [A] polymer component. Part, more preferably 3 to 20 parts by mass. When the amount of the compound [C] used is less than 0.1 parts by weight, the desired effect may not be obtained. On the other hand, when the amount exceeds 100 parts by weight, precipitates are produced during storage of the resulting radiation-sensitive resin composition. May occur.
<[D] Compound having cyclic ether group>
The [D] compound is a compound having a cyclic ether group and different from the polymer of the [A] polymer component. When the radiation sensitive resin composition contains the [D] compound, the thermal reactivity of the [D] compound promotes crosslinking of the [A] polymer component and the like, and further increases the hardness of the formed cured film. In addition, the sensitivity of the radiation sensitive resin composition can be increased. In addition, a [C] compound may be used individually or in combination of 2 or more types.
[D]化合物としては、分子内に2個以上のエポキシ基(オキシラニル基、オキセタニル基)を有する化合物であることが好ましい。 [D] The compound is preferably a compound having two or more epoxy groups (oxiranyl group, oxetanyl group) in the molecule.
分子内に2個以上のオキシラニル基を有する化合物としては、例えば、ビスフェノールAジグリシジルエーテル、ビスフェノールFジグリシジルエーテル、ビスフェノールSジグリシジルエーテル、水添ビスフェノールAジグリシジルエーテル、水添ビスフェノールFジグリシジルエーテル、水添ビスフェノールADジグリシジルエーテル等のビスフェノール型ジグリシジルエーテル類;1,4−ブタンジオールジグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、グリセリントリグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル等の多価アルコールのポリグリシジルエーテル類;エチレングリコール、プロピレングリコール、グリセリン等の脂肪族多価アルコールに1種または2種以上のアルキレンオキサイドを付加することにより得られるポリエーテルポリオールのポリグリシジルエーテル類;フェノールノボラック型エポキシ樹脂;クレゾールノボラック型エポキシ樹脂;ポリフェノール型エポキシ樹脂;脂肪族長鎖二塩基酸のジグリシジルエステル類;高級脂肪酸のグリシジルエステル類;脂肪族ポリグリシジルエーテル類;エポキシ化大豆油、エポキシ化アマニ油等が挙げられる。 Examples of the compound having two or more oxiranyl groups in the molecule include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, and hydrogenated bisphenol F diglycidyl ether. Bisphenol type diglycidyl ethers such as hydrogenated bisphenol AD diglycidyl ether; 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, polyethylene Polyglycidyl ethers of polyhydric alcohols such as glycol diglycidyl ether and polypropylene glycol diglycidyl ether; ethylene glycol Polyglycidyl ethers of polyether polyols obtained by adding one or more alkylene oxides to aliphatic polyhydric alcohols such as ruthenium, propylene glycol and glycerin; phenol novolac type epoxy resins; cresol novolac type epoxy resins A polyphenol type epoxy resin; diglycidyl esters of aliphatic long-chain dibasic acids; glycidyl esters of higher fatty acids; aliphatic polyglycidyl ethers; epoxidized soybean oil, epoxidized linseed oil, and the like.
分子内に2個以上のオキシラニル基を有する[D]化合物の市販品としては、例えば、
ビスフェノールA型エポキシ樹脂として、エピコート1001、同1002、同1003、同1004、同1007、同1009、同1010、同828(以上、ジャパンエポキシレジン製)等;
ビスフェノールF型エポキシ樹脂として、エピコート807(ジャパンエポキシレジン製)等;
フェノールノボラック型エポキシ樹脂として、エピコート152、同154、同157S65(以上、ジャパンエポキシレジン製)、EPPN201、同202(以上、日本化薬製)等;
クレゾールノボラック型エポキシ樹脂として、EOCN102、同103S、同104S、1020、1025、1027(以上、日本化薬製)、エピコート180S75(ジャパンエポキシレジン製)等;
ポリフェノール型エポキシ樹脂として、エピコート1032H60、同XY−4000(以上、ジャパンエポキシレジン製)等;
環状脂肪族エポキシ樹脂として、CY−175、同177、同179、アラルダイトCY−182、同192、184(以上、チバ・スペシャルティ・ケミカルズ製)、ERL−4234、4299、4221、4206(以上、U.C.C製)、ショーダイン509(昭和電工製)、エピクロン200、同400(以上、大日本インキ製)、エピコート871、同872(以上、ジャパンエポキシレジン製)、ED−5661、同5662(以上、セラニーズコーティング製)等;
脂肪族ポリグリシジルエーテルとして、エポライト100MF(共栄社化学製)、エピオールTMP(日本油脂製)等が挙げられる。
As a commercial item of a [D] compound which has two or more oxiranyl groups in a molecule, for example,
As bisphenol A type epoxy resin, Epicoat 1001, 1002, 1003, 1004, 1007, 1009, 1010, 828 (above, made by Japan Epoxy Resin) and the like;
As bisphenol F type epoxy resin, Epicoat 807 (manufactured by Japan Epoxy Resin) and the like;
As a phenol novolac type epoxy resin, Epicoat 152, 154, 157S65 (above, made by Japan Epoxy Resin), EPPN201, 202 (above, made by Nippon Kayaku), etc .;
As cresol novolac type epoxy resin, EOCN102, 103S, 104S, 1020, 1025, 1027 (manufactured by Nippon Kayaku Co., Ltd.), Epicoat 180S75 (manufactured by Japan Epoxy Resin) and the like;
As a polyphenol type epoxy resin, Epicoat 1032H60, XY-4000 (made by Japan Epoxy Resin) and the like;
Cyclic aliphatic epoxy resins include CY-175, 177, 179, Araldite CY-182, 192, 184 (above, manufactured by Ciba Specialty Chemicals), ERL-4234, 4299, 4221, 4206 (above, U C.C), Shodyne 509 (Showa Denko), Epicron 200, 400 (above, Dainippon Ink), Epicoat 871, 872 (above Japan Epoxy Resin), ED-5661, 5562 (Celanese coating)
Examples of the aliphatic polyglycidyl ether include Epolite 100MF (manufactured by Kyoeisha Chemical Co., Ltd.) and Epiol TMP (manufactured by NOF Corporation).
分子内に2個以上のオキセタニル基を有する[D]化合物としては、例えば、イソフタル酸=ビス[(3−エチルオキセタン−3−イル)メチル]、1,4−ビス[(3−エチルオキセタン−3−イル)メトキシメチル]ベンゼン、1,4−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]ベンゼン、ジ[1−エチル−(3−オキセタニル)メチル]エーテル(別名:ビス(3−エチル−3−オキセタニルメチル)エーテル)、3,7−ビス(3−オキセタニル)−5−オキサ−ノナン、3,3’−[1,3−(2−メチレニル)プロパンジイルビス(オキシメチレン)]ビス−(3−エチルオキセタン)、1,2−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]エタン、1,3−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]プロパン、エチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル、ジシクロペンテニルビス(3−エチル−3−オキセタニルメチル)エーテル、トリエチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル、テトラエチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル、トリシクロデカンジイルジメチレン(3−エチル−3−オキセタニルメチル)エーテル、トリメチロールプロパントリス(3−エチル−3−オキセタニルメチル)エーテル、1,4−ビス(3−エチル−3−オキセタニルメトキシ)ブタン、キシレンビスオキセタン、1,6−ビス(3−エチル−3−オキセタニルメトキシ)ヘキサン、ペンタエリスリトールトリス(3−エチル−3−オキセタニルメチル)エーテル、ペンタエリスリトールテトラキス(3−エチル−3−オキセタニルメチル)エーテル、ポリエチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル、ジペンタエリスリトールヘキサキス(3−エチル−3−オキセタニルメチル)エーテル、ジペンタエリスリトールペンタキス(3−エチル−3−オキセタニルメチル)エーテル、ジペンタエリスリトールテトラキス(3−エチル−3−オキセタニルメチル)エーテル、カプロラクトン変性ジペンタエリスリトールヘキサキス(3−エチル−3−オキセタニルメチル)エーテル、カプロラクトン変性ジペンタエリスリトールペンタキス(3−エチル−3−オキセタニルメチル)エーテル、ジトリメチロールプロパンテトラキス(3−エチル−3−オキセタニルメチル)エーテル、EO変性ビスフェノールAビス(3−エチル−3−オキセタニルメチル)エーテル、PO変性ビスフェノールAビス(3−エチル−3−オキセタニルメチル)エーテル、EO変性水添ビスフェノールAビス(3−エチル−3−オキセタニルメチル)エーテル、PO変性水添ビスフェノールAビス(3−エチル−3−オキセタニルメチル)エーテル、EO変性ビスフェノールF(3−エチル−3−オキセタニルメチル)エーテル等が挙げられる。 Examples of the [D] compound having two or more oxetanyl groups in the molecule include isophthalic acid = bis [(3-ethyloxetane-3-yl) methyl], 1,4-bis [(3-ethyloxetane- 3-yl) methoxymethyl] benzene, 1,4-bis [(3-ethyl-3-oxetanylmethoxy) methyl] benzene, di [1-ethyl- (3-oxetanyl) methyl] ether (also known as bis (3- Ethyl-3-oxetanylmethyl) ether), 3,7-bis (3-oxetanyl) -5-oxa-nonane, 3,3 ′-[1,3- (2-methylenyl) propanediylbis (oxymethylene)] Bis- (3-ethyloxetane), 1,2-bis [(3-ethyl-3-oxetanylmethoxy) methyl] ethane, 1,3-bis [(3-ethyl-3-oxeta) Rumethoxy) methyl] propane, ethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, dicyclopentenylbis (3-ethyl-3-oxetanylmethyl) ether, triethyleneglycolbis (3-ethyl-3-oxetanylmethyl) ) Ether, tetraethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, tricyclodecanediyldimethylene (3-ethyl-3-oxetanylmethyl) ether, trimethylolpropane tris (3-ethyl-3-oxetanylmethyl) ) Ether, 1,4-bis (3-ethyl-3-oxetanylmethoxy) butane, xylenebisoxetane, 1,6-bis (3-ethyl-3-oxetanylmethoxy) hexane, pentaerythritol tris (3-ethyl-3) Oxetanylmethyl) ether, pentaerythritol tetrakis (3-ethyl-3-oxetanylmethyl) ether, polyethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol hexakis (3-ethyl-3-oxetanylmethyl) Ether, dipentaerythritol pentakis (3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol tetrakis (3-ethyl-3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol hexakis (3-ethyl-3-oxetanyl) Methyl) ether, caprolactone-modified dipentaerythritol pentakis (3-ethyl-3-oxetanylmethyl) ether, ditrimethylolpropane tetrakis (3-ethyl- 3-oxetanylmethyl) ether, EO-modified bisphenol A bis (3-ethyl-3-oxetanylmethyl) ether, PO-modified bisphenol A bis (3-ethyl-3-oxetanylmethyl) ether, EO-modified hydrogenated bisphenol A bis (3 -Ethyl-3-oxetanylmethyl) ether, PO-modified hydrogenated bisphenol A bis (3-ethyl-3-oxetanylmethyl) ether, EO-modified bisphenol F (3-ethyl-3-oxetanylmethyl) ether, and the like.
これらの中で、[D]化合物としては、分子内に2個以上のオキセタニル基を有する化合物が好ましく、イソフタル酸=ビス[(3−エチルオキセタン−3−イル)メチル]、1,4−ビス[(3−エチルオキセタン−3−イル)メトキシメチル]ベンゼンがより好ましい。 Among these, as the [D] compound, a compound having two or more oxetanyl groups in the molecule is preferable, and isophthalic acid = bis [(3-ethyloxetane-3-yl) methyl], 1,4-bis [(3-Ethyloxetane-3-yl) methoxymethyl] benzene is more preferred.
[D]化合物の含有量としては、[A]重合体成分100質量部に対して、0.5質量部以上100質量部以下であり、1質量部以上50質量部以下が好ましく、10質量部以上25質量部以下がより好ましい。[D]化合物の含有量を上記範囲とすることで、形成される硬化膜の硬度をより高めることができると共に、当該感放射線性樹脂組成物の感度をより高めることができる。
<[E]酸化防止剤>
[E]酸化防止剤は、露光若しくは加熱により発生したラジカルの捕捉により、又は酸化によって生成した過酸化物の分解により、重合体分子の結合の解裂を抑制する成分である。当該感放射線性樹脂組成物が[E]酸化防止剤を含有することで、形成される硬化膜中における重合体分子の解裂劣化が抑制され、例えば、耐光性等を向上させることができる。なお、[E]酸化防止剤は、単独で又は2種以上を組み合わせて用いてもよい。
[D] The content of the compound is 0.5 to 100 parts by weight, preferably 1 to 50 parts by weight, and preferably 10 parts by weight with respect to 100 parts by weight of the polymer component [A]. More preferred is 25 parts by mass or less. [D] By making content of a compound into the said range, while being able to raise the hardness of the cured film formed more, the sensitivity of the said radiation sensitive resin composition can be raised more.
<[E] Antioxidant>
[E] Antioxidant is a component that suppresses the breakage of the bond of the polymer molecule by capturing radicals generated by exposure or heating or by decomposing a peroxide generated by oxidation. When the radiation sensitive resin composition contains the [E] antioxidant, the degradation degradation of the polymer molecules in the formed cured film is suppressed, and for example, the light resistance and the like can be improved. In addition, you may use [E] antioxidant individually or in combination of 2 or more types.
[E]酸化防止剤としては、例えば、ヒンダードフェノール構造を有する化合物、ヒンダードアミン構造を有する化合物、アルキルホスファイト構造を有する化合物、チオエーテル構造を有する化合物等が挙げられる。これらの中で、[E]酸化防止剤は、ヒンダードフェノール構造を有することが好ましい。[E]酸化防止剤がヒンダードフェノール構造を有することで、形成される硬化膜中における重合体分子の解裂劣化をより抑制することができる。 [E] Examples of the antioxidant include a compound having a hindered phenol structure, a compound having a hindered amine structure, a compound having an alkyl phosphite structure, and a compound having a thioether structure. Among these, it is preferable that [E] antioxidant has a hindered phenol structure. [E] When the antioxidant has a hindered phenol structure, the degradation degradation of the polymer molecules in the formed cured film can be further suppressed.
上記ヒンダードフェノール構造を有する化合物としては、例えば、ペンタエリスリトールテトラキス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、チオジエチレンビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、オクタデシル−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート、トリス−(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)−イソシアヌレイト、1,3,5−トリメチル−2,4,6−トリス(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)ベンゼン、N,N’−ヘキサン−1,6−ジイルビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニルプロピオンアミド)、3,3’,3’,5’,5’−ヘキサ−tert−ブチル−a,a’,a’−(メシチレン−2,4,6−トリイル)トリ−p−クレゾール、4,6−ビス(オクチルチオメチル)−o−クレゾール、4,6−ビス(ドデシルチオメチル)−o−クレゾール、エチレンビス(オキシエチレン)ビス[3−(5−tert−ブチル−4−ヒドロキシ−m−トリル)プロピオネート、ヘキサメチレンビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、1,3,5−トリス[(4−tert−ブチル−3−ヒドロキシ−2,6−キシリル)メチル]−1,3,5−トリアジン−2,4,6(1H,3H,5H)−トリオン、2,6−ジ−tert−ブチル−4−(4,6−ビス(オクチルチオ)−1,3,5−トリアジン−2−イルアミン)フェノール等が挙げられる。 Examples of the compound having a hindered phenol structure include pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], thiodiethylene bis [3- (3,5-dithione). -Tert-butyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, tris- (3,5-di-tert-butyl-4- Hydroxybenzyl) -isocyanurate, 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, N, N′-hexane-1, 6-diylbis [3- (3,5-di-tert-butyl-4-hydroxyphenylpropionamide) 3,3 ′, 3 ′, 5 ′, 5′-hexa-tert-butyl-a, a ′, a ′-(mesitylene-2,4,6-triyl) tri-p-cresol, 4,6-bis (Octylthiomethyl) -o-cresol, 4,6-bis (dodecylthiomethyl) -o-cresol, ethylenebis (oxyethylene) bis [3- (5-tert-butyl-4-hydroxy-m-tolyl) Propionate, hexamethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 1,3,5-tris [(4-tert-butyl-3-hydroxy-2,6- Xylyl) methyl] -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione, 2,6-di-tert-butyl-4- (4,6-bis (octylthio)- 1,3 5-triazin-2-ylamine) phenol, and the like.
上記ヒンダードフェノール構造を有する化合物の市販品としては、例えば、アデカスタブAO−20、同AO−30、同AO−40、同AO−50、同AO−60、同AO−70、同AO−80、同AO−330(以上、ADEKA製)、sumilizerGM、同GS、同MDP−S、同BBM−S、同WX−R、同GA−80(以上、住友化学製)、IRGANOX1010、同1035、同1076、同1098、同1135、同1330、同1726、同1425WL、同1520L、同245、同259、同3114、同565、IRGAMOD295(以上、チバジャパン製)、ヨシノックスBHT、同BB、同2246G、同425、同250、同930、同SS、同TT、同917、同314(以上、エーピーアイコーポレーション製)等が挙げられる。 Examples of commercially available compounds having the hindered phenol structure include, for example, ADK STAB AO-20, AO-30, AO-40, AO-50, AO-60, AO-70, and AO-80. , AO-330 (above, manufactured by ADEKA), SumilizerGM, GS, MDP-S, BBM-S, WX-R, GA-80 (above, manufactured by Sumitomo Chemical), IRGANOX1010, 1035, 1076, 1098, 1135, 1330, 1726, 1425WL, 1520L, 1525L, 245, 259, 3114, 565, IRGAMOD295 (above, manufactured by Ciba Japan), Yoshinox BHT, BB, 2246G, 425, 250, 930, SS, TT, 917, 314 (above, API Corporation) Shon, Ltd.), and the like.
[E]酸化防止剤としては、ヒンダードフェノール構造を有する化合物の中でも、ペンタエリスリトールテトラキス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、トリス−(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)−イソシアヌレイトがより好ましい。 [E] As an antioxidant, among compounds having a hindered phenol structure, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], tris- (3,5 -Di-tert-butyl-4-hydroxybenzyl) -isocyanurate is more preferred.
[E]酸化防止剤の含有量としては、[A]重合体成分100質量部に対して、0.1質量部以上10質量部以下が好ましく、0.2質量部以上5質量部以下がより好ましい。[E]酸化防止剤の含有量を上記範囲とすることで、形成される硬化膜の解裂劣化を効果的に抑制することができる。
<その他の任意成分>
当該感放射線性樹脂組成物は、上記[A]〜[E]成分に加え、本発明の効果を損なわない範囲で、必要に応じて[F]塩基性化合物、[G]界面活性剤、[H]密着助剤等のその他の任意成分を含有してもよい。各その他の任意成分は、それぞれ単独で又は2種以上を組み合わせて用いてもよい。以下、各成分を詳述する。
<[F]塩基性化合物>
[F]塩基性化合物としては、化学増幅レジストで用いられるものから任意に選択して使用でき、例えば、脂肪族アミン、芳香族アミン、複素環式アミン、4級アンモニウムヒドロキシド、カルボン酸4級アンモニウム塩等が挙げられる。当該感放射線性樹脂組成物が[F]塩基性化合物を含有することで、露光により[B]光酸発生剤から発生した酸の拡散長を適度に制御することができ、パターン現像性を良好にできる。
[E] The content of the antioxidant is preferably 0.1 parts by mass or more and 10 parts by mass or less, and more preferably 0.2 parts by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the polymer component [A]. preferable. [E] By making content of antioxidant into the said range, the cracking degradation of the formed cured film can be suppressed effectively.
<Other optional components>
In addition to the above-mentioned components [A] to [E], the radiation-sensitive resin composition includes [F] a basic compound, [G] a surfactant, and [A] as long as the effects of the present invention are not impaired. H] Other optional components such as an adhesion aid may be contained. Each other optional component may be used alone or in combination of two or more. Hereinafter, each component will be described in detail.
<[F] Basic compound>
[F] The basic compound can be arbitrarily selected from those used in chemically amplified resists, and examples thereof include aliphatic amines, aromatic amines, heterocyclic amines, quaternary ammonium hydroxides, and carboxylic acid quaternary compounds. An ammonium salt etc. are mentioned. When the radiation-sensitive resin composition contains the [F] basic compound, the diffusion length of the acid generated from the [B] photoacid generator by exposure can be appropriately controlled, and the pattern developability is good. Can be.
上記脂肪族アミンとしては、例えば、トリメチルアミン、ジエチルアミン、トリエチルアミン、ジ−n−プロピルアミン、トリ−n−プロピルアミン、ジ−n−ペンチルアミン、トリ−n−ペンチルアミン、ジエタノールアミン、トリエタノールアミン、ジシクロヘキシルアミン、ジシクロヘキシルメチルアミン等が挙げられる。 Examples of the aliphatic amine include trimethylamine, diethylamine, triethylamine, di-n-propylamine, tri-n-propylamine, di-n-pentylamine, tri-n-pentylamine, diethanolamine, triethanolamine, and dicyclohexyl. Examples include amines and dicyclohexylmethylamine.
上記芳香族アミンとしては、例えば、アニリン、ベンジルアミン、N,N−ジメチルアニリン、ジフェニルアミン等が挙げられる。 Examples of the aromatic amine include aniline, benzylamine, N, N-dimethylaniline, diphenylamine and the like.
上記複素環式アミンとしては、例えば、ピリジン、2−メチルピリジン、4−メチルピリジン、2−エチルピリジン、4−エチルピリジン、2−フェニルピリジン、4−フェニルピリジン、N−メチル−4−フェニルピリジン、4−ジメチルアミノピリジン、イミダゾール、ベンズイミダゾール、4−メチルイミダゾール、2−フェニルベンズイミダゾール、2,4,5−トリフェニルイミダゾール、ニコチン、ニコチン酸、ニコチン酸アミド、キノリン、8−オキシキノリン、ピラジン、ピラゾール、ピリダジン、プリン、ピロリジン、ピペリジン、ピペラジン、モルホリン、4−メチルモルホリン、1,5−ジアザビシクロ[4,3,0]−5−ノネン、1,8−ジアザビシクロ[5,3,0]−7ウンデセン等が挙げられる。 Examples of the heterocyclic amine include pyridine, 2-methylpyridine, 4-methylpyridine, 2-ethylpyridine, 4-ethylpyridine, 2-phenylpyridine, 4-phenylpyridine, and N-methyl-4-phenylpyridine. , 4-dimethylaminopyridine, imidazole, benzimidazole, 4-methylimidazole, 2-phenylbenzimidazole, 2,4,5-triphenylimidazole, nicotine, nicotinic acid, nicotinamide, quinoline, 8-oxyquinoline, pyrazine , Pyrazole, pyridazine, purine, pyrrolidine, piperidine, piperazine, morpholine, 4-methylmorpholine, 1,5-diazabicyclo [4,3,0] -5-nonene, 1,8-diazabicyclo [5,3,0]- 7 undecene and the like.
上記4級アンモニウムヒドロキシドとしては、例えば、テトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド、テトラ−n−ブチルアンモニウムヒドロキシド、テトラ−n−ヘキシルアンモニウムヒドロキシド等が挙げられる。 Examples of the quaternary ammonium hydroxide include tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetra-n-butylammonium hydroxide, and tetra-n-hexylammonium hydroxide.
上記カルボン酸4級アンモニウム塩としては、例えば、テトラメチルアンモニウムアセテート、テトラメチルアンモニウムベンゾエート、テトラ−n−ブチルアンモニウムアセテート、テトラ−n−ブチルアンモニウムベンゾエート等が挙げられる。 Examples of the carboxylic acid quaternary ammonium salt include tetramethylammonium acetate, tetramethylammonium benzoate, tetra-n-butylammonium acetate, and tetra-n-butylammonium benzoate.
これらの中で、[F]塩基性化合物としては、複素環式アミンが好ましく、4−ジメチルアミノピリジン、4−メチルイミダゾール、1,5−ジアザビシクロ[4,3,0]−5−ノネン、ジメチルn−ドデシルアミン、トリフェニルスルホニウムサリチレート、2−フェニルベンズイミダゾール等がより好ましい。 Among these, the [F] basic compound is preferably a heterocyclic amine, such as 4-dimethylaminopyridine, 4-methylimidazole, 1,5-diazabicyclo [4,3,0] -5-nonene, dimethyl. n-dodecylamine, triphenylsulfonium salicylate, 2-phenylbenzimidazole and the like are more preferable.
[F]塩基性化合物の含有量としては、[A]重合体成分100質量部に対して、0.001質量部以上1質量部以下が好ましく、0.005質量部以上0.2質量部以下がより好ましい。[F]塩基性化合物の含有量を上記範囲とすることで、パターン現像性がより向上する。
<[G]界面活性剤>
[G]界面活性剤は、当該感放射線性樹脂組成物の塗膜形成性を高める成分である。[G]界面活性剤としては、例えば、フッ素系界面活性剤、シリコーン系界面活性剤等が挙げられる。当該感放射線性樹脂組成物が[G]界面活性剤を含有することで、塗膜の表面平滑性を向上でき、その結果、形成される硬化膜の膜厚均一性をより向上できる。
[F] The content of the basic compound is preferably 0.001 part by mass or more and 1 part by mass or less, and 0.005 part by mass or more and 0.2 part by mass or less with respect to 100 parts by mass of the polymer component [A]. Is more preferable. [F] By making content of a basic compound into the said range, pattern developability improves more.
<[G] Surfactant>
[G] Surfactant is a component that enhances the film-forming property of the radiation-sensitive resin composition. [G] Examples of the surfactant include a fluorine-based surfactant and a silicone-based surfactant. When the said radiation sensitive resin composition contains [G] surfactant, the surface smoothness of a coating film can be improved, As a result, the film thickness uniformity of the formed cured film can be improved more.
上記フッ素系界面活性剤としては、末端、主鎖及び側鎖の少なくともいずれかの部位にフルオロアルキル基及び/又はフルオロアルキレン基を有する化合物が好ましく、例えば、1,1,2,2−テトラフルオロn−オクチル(1,1,2,2−テトラフルオロn−プロピル)エーテル、1,1,2,2−テトラフルオロn−オクチル(n−ヘキシル)エーテル、ヘキサエチレングリコールジ(1,1,2,2,3,3−ヘキサフルオロn−ペンチル)エーテル、オクタエチレングリコールジ(1,1,2,2−テトラフルオロn−ブチル)エーテル、ヘキサプロピレングリコールジ(1,1,2,2,3,3−ヘキサフルオロn−ペンチル)エーテル、オクタプロピレングリコールジ(1,1,2,2−テトラフルオロn−ブチル)エーテル、パーフルオロn−ドデカンスルホン酸ナトリウム、1,1,2,2,3,3−ヘキサフルオロn−デカン、1,1,2,2,3,3,9,9,10,10−デカフルオロn−ドデカン、フルオロアルキルベンゼンスルホン酸ナトリウム、フルオロアルキルリン酸ナトリウム、フルオロアルキルカルボン酸ナトリウム、ジグリセリンテトラキス(フルオロアルキルポリオキシエチレンエーテル)、フルオロアルキルアンモニウムヨージド、フルオロアルキルベタイン、フルオロアルキルポリオキシエチレンエーテル、パーフルオロアルキルポリオキシエタノール、パーフルオロアルキルアルコキシレート、カルボン酸フルオロアルキルエステル等が挙げられる。 As the fluorosurfactant, a compound having a fluoroalkyl group and / or a fluoroalkylene group in at least one of the terminal, main chain and side chain is preferable. For example, 1,1,2,2-tetrafluoro n-octyl (1,1,2,2-tetrafluoro n-propyl) ether, 1,1,2,2-tetrafluoro n-octyl (n-hexyl) ether, hexaethylene glycol di (1,1,2, , 2,3,3-hexafluoro n-pentyl) ether, octaethylene glycol di (1,1,2,2-tetrafluoro n-butyl) ether, hexapropylene glycol di (1,1,2,2,3) , 3-Hexafluoron-pentyl) ether, octapropylene glycol di (1,1,2,2-tetrafluoron-butyl) ether , Sodium perfluoro n-dodecanesulfonate, 1,1,2,2,3,3-hexafluoro n-decane, 1,1,2,2,3,3,9,9,10,10-decafluoro n-dodecane, sodium fluoroalkylbenzenesulfonate, sodium fluoroalkylphosphate, sodium fluoroalkylcarboxylate, diglycerin tetrakis (fluoroalkylpolyoxyethylene ether), fluoroalkylammonium iodide, fluoroalkylbetaine, fluoroalkylpolyoxyethylene ether Perfluoroalkyl polyoxyethanol, perfluoroalkyl alkoxylate, carboxylic acid fluoroalkyl ester, and the like.
上記フッ素系界面活性剤の市販品としては、例えば、BM−1000、BM−1100(以上、BM CHEMIE製)、メガファックF142D、同F172、同F173、同F183、同F178、同F191、同F471、同F476(以上、大日本インキ化学工業製)、フロラードFC−170C、同FC−171、同FC−430、同FC−431(以上、住友スリーエム製)、サーフロンS−112、同S−113、同S−131、同S−141、同S−145、同S−382、同SC−101、同SC−102、同SC−103、同SC−104、同SC−105、同SC−106(以上、旭硝子製)、エフトップEF301、同EF303、同EF352(以上、新秋田化成製)、フタージェントFT−100、同FT−110、同FT−140A、同FT−150、同FT−250、同FT−251、同FT−300、同FT−310、同FT−400S、同FTX−218、同FT−251(以上、ネオス製)等が挙げられる。 Examples of commercially available fluorosurfactants include BM-1000, BM-1100 (manufactured by BM CHEMIE), MegaFuck F142D, F172, F173, F183, F178, F191, F191, and F471. , F476 (above, manufactured by Dainippon Ink and Chemicals), Fluorard FC-170C, FC-171, FC-430, FC-431 (above, manufactured by Sumitomo 3M), Surflon S-112, S-113 S-131, S-141, S-145, S-382, SC-101, SC-102, SC-103, SC-104, SC-105, SC-106 (Above, manufactured by Asahi Glass Co., Ltd.), F-top EF301, EF303, EF352 (above, manufactured by Shin-Akita Kasei), FT FT-100, FT-1 0, FT-140A, FT-150, FT-250, FT-251, FT-300, FT-310, FT-400S, FTX-218, FT-251 (above, Neos Manufactured) and the like.
上記シリコーン系界面活性剤の市販品としては、例えば、トーレシリコーンDC3PA、同DC7PA、同SH11PA、同SH21PA、同SH28PA、同SH29PA、同SH30PA、同SH−190、同SH−193、同SZ−6032、同SF−8428、同DC−57、同DC−190、SH 8400 FLUID(以上、東レダウコーニングシリコーン製)、TSF−4440、TSF−4300、TSF−4445、TSF−4446、TSF−4460、TSF−4452(以上、GE東芝シリコーン製)、オルガノシロキサンポリマーKP341(信越化学工業製)等が挙げられる。 Examples of commercially available silicone surfactants include Toray Silicone DC3PA, DC7PA, SH11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH-190, SH-193, and SZ-6032. SF-8428, DC-57, DC-190, DC-190, SH 8400 FLUID (manufactured by Toray Dow Corning Silicone), TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, TSF -4552 (manufactured by GE Toshiba Silicone), organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.) and the like.
[G]界面活性剤の含有量としては、[A]重合体成分100質量部に対して、0.01質量部以上2質量部以下が好ましく、0.05質量部以上1質量部以下がより好ましい。[G]界面活性剤の含有量を上記範囲とすることで、形成される塗膜の膜厚均一性をより向上できる。
<[H]密着助剤>
[H]密着助剤は、基板となる無機物、例えばシリコーン、酸化シリコーン、窒化シリコーン等のシリコーン化合物、金、銅、アルミニウム等の金属と硬化膜との接着性を向上させる成分である。[H]密着助剤としては、官能性シランカップリング剤が好ましい。上記官能性シランカップリング剤としては、例えば、カルボキシ基、メタクリロイル基、イソシアネート基、エポキシ基(好ましくはオキシラニル基)、チオール基等の反応性置換基を有するシランカップリング剤等が挙げられる。
[G] The content of the surfactant is preferably 0.01 parts by mass or more and 2 parts by mass or less, and more preferably 0.05 parts by mass or more and 1 part by mass or less with respect to 100 parts by mass of the polymer component [A]. preferable. [G] By making content of surfactant into the said range, the film thickness uniformity of the coating film formed can be improved more.
<[H] Adhesion aid>
[H] The adhesion assistant is a component that improves the adhesion between a cured film and an inorganic substance serving as a substrate, for example, a silicone compound such as silicone, silicone oxide, or silicon nitride, or a metal such as gold, copper, or aluminum. [H] The adhesion assistant is preferably a functional silane coupling agent. As said functional silane coupling agent, the silane coupling agent etc. which have reactive substituents, such as a carboxy group, a methacryloyl group, an isocyanate group, an epoxy group (preferably oxiranyl group), a thiol group, etc. are mentioned, for example.
上記官能性シランカップリング剤としては、例えば、トリメトキシシリル安息香酸、γ−メタクリロキシプロピルトリメトキシシラン、ビニルトリアセトキシシラン、ビニルトリメトキシシラン、γ−イソシアネートプロピルトリエトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルアルキルジアルコキシシラン、γ−クロロプロピルトリアルコキシシラン、γ−メルカプトプロピルトリアルコキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン等が挙げられる。これらの中で、官能性シランカップリング剤としては、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルアルキルジアルコキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、γ−メタクリロキシプロピルトリメトキシシランが好ましい。 Examples of the functional silane coupling agent include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatopropyltriethoxysilane, and γ-glycidoxy. Examples include propyltrimethoxysilane, γ-glycidoxypropylalkyldialkoxysilane, γ-chloropropyltrialkoxysilane, γ-mercaptopropyltrialkoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and the like. . Among these, as the functional silane coupling agent, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylalkyldialkoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-Methacryloxypropyltrimethoxysilane is preferred.
[H]密着助剤の含有量としては、[A]重合体成分100質量部に対して、0.5質量部以上20質量部以下が好ましく、1質量部以上10質量部以下がより好ましい。[H]密着助剤の含有量を上記範囲とすることで、形成される硬化膜と基板との密着性がより改善される。
<感放射線性樹脂組成物の調製方法>
当該感放射線性樹脂組成物は、溶媒に[A]重合体、[B]光酸発生剤、[C]化合物、必要に応じて好適成分、その他の任意成分を混合することによって溶解又は分散させた状態に調製される。例えば、溶媒中で各成分を所定の割合で混合することにより、当該感放射線性樹脂組成物を調製できる。
[H] The content of the adhesion assistant is preferably 0.5 parts by mass or more and 20 parts by mass or less, and more preferably 1 part by mass or more and 10 parts by mass or less with respect to 100 parts by mass of the polymer component [A]. [H] By setting the content of the adhesion assistant in the above range, the adhesion between the formed cured film and the substrate is further improved.
<Method for preparing radiation-sensitive resin composition>
The radiation-sensitive resin composition is dissolved or dispersed by mixing [A] polymer, [B] photoacid generator, [C] compound, if necessary, suitable components and other optional components in a solvent. Prepared. For example, the said radiation sensitive resin composition can be prepared by mixing each component in a predetermined ratio in a solvent.
溶媒としては、各成分を均一に溶解又は分散し、各成分と反応しないものが好適に用いられる。上記溶媒としては、例えば、アルコール類、エーテル類、グリコールエーテル、エチレングリコールアルキルエーテルアセテート、ジエチレングリコールアルキルエーテル、プロピレングリコールモノアルキルエーテル、プロピレングリコールモノアルキルエーテルアセテート、プロピレングリコールモノアルキルエーテルプロピオネート、芳香族炭化水素類、ケトン類、他のエステル類等が挙げられる。 As the solvent, a solvent in which each component is uniformly dissolved or dispersed and does not react with each component is preferably used. Examples of the solvent include alcohols, ethers, glycol ethers, ethylene glycol alkyl ether acetates, diethylene glycol alkyl ethers, propylene glycol monoalkyl ethers, propylene glycol monoalkyl ether acetates, propylene glycol monoalkyl ether propionates, and aromatics. Examples include hydrocarbons, ketones, and other esters.
上記アルコール類としては、例えば、メタノール、エタノール、ベンジルアルコール、2−フェニルエチルアルコール、3−フェニル−1−プロパノール等が挙げられる。 Examples of the alcohols include methanol, ethanol, benzyl alcohol, 2-phenylethyl alcohol, and 3-phenyl-1-propanol.
上記エーテル類としては、例えば、テトラヒドロフラン等が挙げられる。 Examples of the ethers include tetrahydrofuran.
上記グリコールエーテルとして、例えば、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル等が挙げられる。 Examples of the glycol ether include ethylene glycol monomethyl ether and ethylene glycol monoethyl ether.
上記エチレングリコールアルキルエーテルアセテートとしては、例えば、メチルセロソルブアセテート、エチルセロソルブアセテート、エチレングリコールモノブチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート等が挙げられる。 Examples of the ethylene glycol alkyl ether acetate include methyl cellosolve acetate, ethyl cellosolve acetate, ethylene glycol monobutyl ether acetate, and ethylene glycol monoethyl ether acetate.
上記ジエチレングリコールアルキルエーテルとしては、例えば、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールエチルメチルエーテル等が挙げられる。 Examples of the diethylene glycol alkyl ether include diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and diethylene glycol ethyl methyl ether.
上記プロピレングリコールモノアルキルエーテルとしては、例えば、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル等が挙げられる。 Examples of the propylene glycol monoalkyl ether include propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether and the like.
上記プロピレングリコールモノアルキルエーテルアセテートとしては、例えば、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテルアセテート、プロピレングリコールモノブチルエーテルアセテート等が挙げられる。 Examples of the propylene glycol monoalkyl ether acetate include propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate and the like.
上記プロピレングリコールモノアルキルエーテルプロピオネートとしては、例えば、プロピレンモノグリコールメチルエーテルプロピオネート、プロピレングリコールモノエチルエーテルプロピオネート、プロピレングリコールモノプロピルエーテルプロピオネート、プロピレングリコールモノブチルエーテルプロピオネート等が挙げられる。 Examples of the propylene glycol monoalkyl ether propionate include propylene monoglycol methyl ether propionate, propylene glycol monoethyl ether propionate, propylene glycol monopropyl ether propionate, and propylene glycol monobutyl ether propionate. Can be mentioned.
上記芳香族炭化水素類としては、例えば、トルエン、キシレン等が挙げられる。 Examples of the aromatic hydrocarbons include toluene and xylene.
上記ケトン類としては、例えば、メチルエチルケトン、シクロヘキサノン、4−ヒドロキシ−4−メチル−2−ペンタノン等が挙げられる。 Examples of the ketones include methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, and the like.
上記他のエステル類としては、例えば、酢酸メチル、酢酸エチル、酢酸プロピル、酢酸ブチル、2−ヒドロキシプロピオン酸エチル、2−ヒドロキシ−2−メチルプロピオン酸メチル、2−ヒドロキシ−2−メチルプロピオン酸エチル、ヒドロキシ酢酸メチル、ヒドロキシ酢酸エチル、ヒドロキシ酢酸ブチル、乳酸メチル、乳酸エチル、乳酸プロピル、乳酸ブチル、3−ヒドロキシプロピオン酸メチル、3−ヒドロキシプロピオン酸エチル、3−ヒドロキシプロピオン酸プロピル、3−ヒドロキシプロピオン酸ブチル、2−ヒドロキシ−3−メチルブタン酸メチル、メトキシ酢酸メチル、メトキシ酢酸エチル、メトキシ酢酸プロピル、メトキシ酢酸ブチル、エトキシ酢酸メチル、エトキシ酢酸エチル、エトキシ酢酸プロピル、エトキシ酢酸ブチル、プロポキシ酢酸メチル、プロポキシ酢酸エチル、プロポキシ酢酸プロピル、プロポキシ酢酸ブチル、ブトキシ酢酸メチル、ブトキシ酢酸エチル、ブトキシ酢酸プロピル、ブトキシ酢酸ブチル、2−メトキシプロピオン酸メチル、2−メトキシプロピオン酸エチル、2−メトキシプロピオン酸プロピル、2−メトキシプロピオン酸ブチル、2−エトキシプロピオン酸メチル、2−エトキシプロピオン酸エチル、2−エトキシプロピオン酸プロピル、2−エトキシプロピオン酸ブチル、2−ブトキシプロピオン酸メチル、2−ブトキシプロピオン酸エチル、2−ブトキシプロピオン酸プロピル、2−ブトキシプロピオン酸ブチル、3−メトキシプロピオン酸メチル、3−メトキシプロピオン酸エチル、3−メトキシプロピオン酸プロピル、3−メトキシプロピオン酸ブチル、3−エトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、3−エトキシプロピオン酸プロピル、3−エトキシプロピオン酸ブチル、3−プロポキシプロピオン酸メチル、3−プロポキシプロピオン酸エチル、3−プロポキシプロピオン酸プロピル、3−プロポキシプロピオン酸ブチル、3−ブトキシプロピオン酸メチル、3−ブトキシプロピオン酸エチル、3−ブトキシプロピオン酸プロピル、3−ブトキシプロピオン酸ブチル等が挙げられる。 Examples of the other esters include methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl 2-hydroxypropionate, methyl 2-hydroxy-2-methylpropionate, and ethyl 2-hydroxy-2-methylpropionate. , Methyl hydroxyacetate, ethyl hydroxyacetate, hydroxybutyl acetate, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate, propyl 3-hydroxypropionate, 3-hydroxypropion Acid butyl, methyl 2-hydroxy-3-methylbutanoate, methyl methoxyacetate, ethyl methoxyacetate, propyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, propyl ethoxyacetate, , Methyl propoxyacetate, ethyl propoxyacetate, propylpropoxyacetate, butyl propoxyacetate, methyl butoxyacetate, ethyl butoxyacetate, propylbutoxyacetate, butylbutoxyacetate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate Propyl methoxypropionate, butyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, propyl 2-ethoxypropionate, butyl 2-ethoxypropionate, methyl 2-butoxypropionate, 2-butoxy Ethyl propionate, propyl 2-butoxypropionate, butyl 2-butoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, -Butyl methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, propyl 3-ethoxypropionate, butyl 3-ethoxypropionate, methyl 3-propoxypropionate, ethyl 3-propoxypropionate, 3- Examples include propyl propoxypropionate, butyl 3-propoxypropionate, methyl 3-butoxypropionate, ethyl 3-butoxypropionate, propyl 3-butoxypropionate, and butyl 3-butoxypropionate.
これらの溶媒の中で、エチレングリコールアルキルエーテルアセテート、ジエチレングリコールアルキルエーテル、プロピレングリコールモノアルキルエーテル、プロピレングリコールモノアルキルエーテルアセテート、メトキシ酢酸ブチルが好ましく、ジエチレングリコールジメチルエーテル、ジエチレングリコールエチルメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテル、メトキシ酢酸ブチルがより好ましく、ジエチレングリコールエチルメチルエーテルがさらに好ましい。
<硬化膜の形成方法>
当該感放射線性樹脂組成物は、硬化膜の形成に好適に用いることができる。
Among these solvents, ethylene glycol alkyl ether acetate, diethylene glycol alkyl ether, propylene glycol monoalkyl ether, propylene glycol monoalkyl ether acetate and butyl methoxyacetate are preferred, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, propylene glycol monomethyl ether acetate, Propylene glycol monomethyl ether and butyl methoxyacetate are more preferable, and diethylene glycol ethyl methyl ether is more preferable.
<Method for forming cured film>
The said radiation sensitive resin composition can be used suitably for formation of a cured film.
本発明の硬化膜の形成方法は、
(1)当該感放射線性樹脂組成物を用い、基板上に塗膜を形成する工程、
(2)上記塗膜の少なくとも一部に放射線を照射する工程、
(3)上記放射線が照射された塗膜を現像する工程、及び
(4)上記現像された塗膜を加熱する工程
を有する。
The method for forming the cured film of the present invention is as follows.
(1) The process of forming a coating film on a board | substrate using the said radiation sensitive resin composition,
(2) A step of irradiating at least a part of the coating film with radiation,
(3) a step of developing the coating film irradiated with the radiation; and (4) a step of heating the developed coating film.
当該形成方法によると、パターン形状の安定性が高い硬化膜を形成できる。また、未露光部の膜厚変化量を抑制できることから、結果として生産プロセスマージンを向上でき、歩留まりの向上を達成できる。さらに、感光性を利用した露光、現像、加熱によりパターンを形成することによって、容易に微細かつ精巧なパターンを有する硬化膜を形成できる。
[工程(1)]
本工程では、当該感放射線性樹脂組成物を用い、基板上に塗布して塗膜を形成する。好ましくは塗布面をプレベークすることによって溶媒を除去する。
上記基板としては、例えば、ガラス、石英、シリコーン、樹脂等が挙げられる。上記樹脂としては、例えば、ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリエーテルスルホン、ポリカーボネート、ポリイミド、環状オレフィンの開環重合体及びその水素添加物等が挙げられる。プレベークの条件としては、各成分の種類、配合割合等によっても異なるが、70℃〜120℃、1分〜10分間程度とすることができる。
[工程(2)]
本工程では、上記形成された塗膜の少なくとも一部に放射線を照射し露光する。露光する際には、通常所定のパターンを有するフォトマスクを介して露光する。露光に使用される放射線としては、波長が190nm〜450nmの範囲にある放射線が好ましく、365nmの紫外線を含む放射線がより好ましい。露光量としては、放射線の波長365nmにおける強度を、照度計(OAI model356、OAI Optical Associates製)により測定した値で、500J/m2〜6,000J/m2が好ましく、1,500J/m2〜1,800J/m2がより好ましい。
[工程(3)]
本工程では、上記放射線が照射された塗膜を現像する。露光後の塗膜を現像することにより、不要な部分(放射線の照射部分)を除去して所定のパターンを形成する。この現像工程に使用される現像液としては、アルカリ性の水溶液が好ましい。アルカリとしては、例えば、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、ケイ酸ナトリウム、メタケイ酸ナトリウム、アンモニア等の無機アルカリ;テトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド等の4級アンモニウム塩、ケトン系有機溶剤、アルコール系有機溶剤等が挙げられる。
アルカリ水溶液には、メタノール、エタノール等の水溶性有機溶媒や界面活性剤を適当量添加して使用することもできる。アルカリ水溶液におけるアルカリの濃度しては、適当な現像性を得る観点から、0.1質量%以上5質量%以下が好ましい。現像方法としては、例えば、液盛り法、ディッピング法、揺動浸漬法、シャワー法等が挙げられる。現像時間としては、当該感放射線性樹脂組成物の組成によって異なるが、10秒〜180秒間程度である。このような現像処理に続いて、例えば流水洗浄を30秒〜90秒間行った後、例えば圧縮空気や圧縮窒素で風乾させることによって、所望のパターンを形成できる。
現像前の塗膜の膜厚T0に対する現像後の膜厚T1の膜厚変化率は、90%以上であることが好ましい。上述したように、当該感放射線性樹脂組成物を用いた当該形成方法によると、現像時間に対する未露光部の膜厚変化量を抑制でき、現像後の膜厚は、現像前の膜厚の90%以上を維持することができる。
[工程(4)]
本工程では、上記現像された塗膜を加熱する。加熱には、ホットプレート、オーブン等の加熱装置を用い、パターニングされた薄膜を加熱することで、[A]重合体成分の硬化反応を促進して、硬化膜を形成することができる。加熱温度としては、例えば、120℃〜250℃程度である。加熱時間としては、加熱機器の種類により異なるが、例えば、ホットプレートでは5分〜30分間程度、オーブンでは30分〜90分間程度である。また、2回以上の加熱工程を行うステップベーク法等を用いることもできる。このようにして、目的とする硬化膜に対応するパターン状薄膜を基板の表面上に形成できる。形成された硬化膜の膜厚としては、0.1μm〜8μmが好ましく、0.1μm〜6μmがより好ましい。
According to the forming method, a cured film having high pattern shape stability can be formed. Further, since the amount of change in the film thickness of the unexposed portion can be suppressed, the production process margin can be improved as a result, and the yield can be improved. Furthermore, a cured film having a fine and elaborate pattern can be easily formed by forming a pattern by exposure, development and heating utilizing photosensitivity.
[Step (1)]
In this step, the radiation-sensitive resin composition is used and applied onto a substrate to form a coating film. Preferably, the solvent is removed by prebaking the coated surface.
Examples of the substrate include glass, quartz, silicone, and resin. Examples of the resin include polyethylene terephthalate, polybutylene terephthalate, polyethersulfone, polycarbonate, polyimide, a ring-opening polymer of cyclic olefin, and a hydrogenated product thereof. As prebaking conditions, although it changes also with kinds, compounding ratios, etc. of each component, it can be set as 70 degreeC-120 degreeC, about 1 minute-10 minutes.
[Step (2)]
In this step, at least a part of the formed coating film is exposed to radiation and exposed. When exposing, it exposes normally through the photomask which has a predetermined pattern. As the radiation used for exposure, radiation having a wavelength in the range of 190 nm to 450 nm is preferable, and radiation containing ultraviolet light of 365 nm is more preferable. Energy of exposure intensity at the wavelength 365nm radiation, by the value measured by luminometer (OAI model356, OAI Optical Ltd. Associates), is preferably 500J / m 2 ~6,000J / m 2 , 1,500J / m 2 ˜1,800 J / m 2 is more preferable.
[Step (3)]
In this step, the coating film irradiated with the radiation is developed. By developing the coated film after exposure, unnecessary portions (radiation irradiated portions) are removed to form a predetermined pattern. As the developer used in this development step, an alkaline aqueous solution is preferable. Examples of the alkali include inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, and ammonia; quaternary ammonium salts such as tetramethylammonium hydroxide and tetraethylammonium hydroxide, and ketones. Examples thereof include organic solvents and alcohol-based organic solvents.
An appropriate amount of a water-soluble organic solvent such as methanol or ethanol, or a surfactant can be added to the alkaline aqueous solution. The concentration of alkali in the aqueous alkali solution is preferably from 0.1% by mass to 5% by mass from the viewpoint of obtaining appropriate developability. Examples of the developing method include a liquid piling method, a dipping method, a rocking dipping method, a shower method, and the like. The development time varies depending on the composition of the radiation sensitive resin composition, but is about 10 seconds to 180 seconds. Subsequent to such development processing, for example, washing with running water is performed for 30 seconds to 90 seconds, and then a desired pattern can be formed by, for example, air drying with compressed air or compressed nitrogen.
Thickness change rate of the thickness T 1 of the after development with respect to the film thickness T 0 of the coating film before development is preferably 90% or more. As described above, according to the forming method using the radiation-sensitive resin composition, the amount of change in the film thickness of the unexposed portion with respect to the development time can be suppressed, and the film thickness after development is 90% of the film thickness before development. % Or more can be maintained.
[Step (4)]
In this step, the developed coating film is heated. For heating, the patterned thin film is heated using a heating device such as a hot plate or an oven, whereby the curing reaction of the polymer component [A] can be promoted to form a cured film. As heating temperature, it is about 120 to 250 degreeC, for example. The heating time varies depending on the type of the heating device, but is, for example, about 5 to 30 minutes for a hot plate and about 30 to 90 minutes for an oven. Moreover, the step baking method etc. which perform a heating process 2 times or more can also be used. In this way, a patterned thin film corresponding to the desired cured film can be formed on the surface of the substrate. The film thickness of the formed cured film is preferably 0.1 μm to 8 μm, more preferably 0.1 μm to 6 μm.
<硬化膜>
本発明の硬化膜は、当該感放射線性樹脂組成物から形成される。当該硬化膜は、当該感放射線性樹脂組成物から形成されているため、高い表面硬度、耐熱性等を有し、かつ膜厚の変化が少ない。当該硬化膜は、上記性質を有しているため、例えば、表示素子の層間絶縁膜、スペーサー、保護膜、カラーフィルタ用着色パターン等として好適である。なお、当該硬化膜の形成方法としては特に限定されないが、上述の当該硬化膜の形成方法を用いることが好ましい。
<Curing film>
The cured film of the present invention is formed from the radiation sensitive resin composition. Since the said cured film is formed from the said radiation sensitive resin composition, it has high surface hardness, heat resistance, etc., and there are few changes of a film thickness. Since the cured film has the above properties, it is suitable as, for example, an interlayer insulating film of a display element, a spacer, a protective film, a color filter coloring pattern, or the like. In addition, although it does not specifically limit as a formation method of the said cured film, It is preferable to use the formation method of the said cured film mentioned above.
<表示素子>
本発明の表示素子は、当該硬化膜を備えている。当該表示素子は、例えば、後述する液晶セル、偏光板等により構成されている。当該表示素子は、当該硬化膜を備えているため、例えば、耐熱性等の信頼性に優れる。
<Display element>
The display element of the present invention includes the cured film. The display element includes, for example, a liquid crystal cell, a polarizing plate, and the like which will be described later. Since the display element includes the cured film, the display element is excellent in reliability such as heat resistance.
当該表示素子の製造方法としては、まず片面に透明導電膜(電極)を有する透明基板を一対(2枚)準備し、そのうちの一枚の基板の透明導電膜上に、当該感放射線性樹脂組成物を用い、上述の硬化膜の形成方法に従って、層間絶縁膜、スペーサー若しくは保護膜又はその双方を形成する。次いで、これらの基板の透明導電膜及びスペーサー又は保護膜上に液晶配向能を有する配向膜を形成する。これら基板を、その配向膜が形成された側の面を内側にして、それぞれの配向膜の液晶配向方向が直交又は逆平行となるように一定の間隙(セルギャップ)を介して対向配置し、基板の表面(配向膜)及びスペーサーにより区画されたセルギャップ内に液晶を充填し、充填孔を封止して液晶セルを構成する。そして、液晶セルの両外表面に、偏光板を、その偏光方向が当該基板の一面に形成された配向膜の液晶配向方向と一致又は直交するように貼り合わせることにより、本発明の表示素子が得られる。 As a method for manufacturing the display element, first, a pair (two) of transparent substrates having a transparent conductive film (electrode) on one side is prepared, and the radiation-sensitive resin composition is formed on the transparent conductive film of one of the substrates. Using an object, an interlayer insulating film, a spacer, a protective film, or both are formed according to the method for forming a cured film described above. Next, an alignment film having liquid crystal alignment ability is formed on the transparent conductive film and the spacer or protective film of these substrates. These substrates are arranged facing each other with a certain gap (cell gap) so that the liquid crystal alignment direction of each alignment film is orthogonal or antiparallel, with the surface on which the alignment film is formed inside. A liquid crystal is filled in the cell gap defined by the surface of the substrate (alignment film) and the spacer, and the filling hole is sealed to constitute a liquid crystal cell. Then, the display element of the present invention is bonded to both outer surfaces of the liquid crystal cell such that the polarizing direction is aligned or orthogonal to the liquid crystal alignment direction of the alignment film formed on one surface of the substrate. can get.
他の表示素子の製造方法としては、上記製造方法と同様にして透明導電膜と、層間絶縁膜、保護膜又はスペーサー又はその双方と、配向膜とを形成した一対の透明基板を準備する。その後、一方の基板の端部に沿って、ディスペンサーを用いて紫外線硬化型シール剤を塗布し、次いで液晶ディスペンサーを用いて微小液滴状に液晶を滴下し、真空下で両基板の貼り合わせを行う。そして、上記のシール剤部に、高圧水銀ランプを用いて紫外線を照射して両基板を封止する。最後に、液晶セルの両外表面に偏光板を貼り合わせることにより、本発明の表示素子が得られる。 As another method for manufacturing a display element, a pair of transparent substrates on which a transparent conductive film, an interlayer insulating film, a protective film, a spacer, or both, and an alignment film are formed are prepared in the same manner as the above manufacturing method. After that, along the edge of one of the substrates, an ultraviolet curable sealant is applied using a dispenser, then the liquid crystal is dropped into a fine droplet using a liquid crystal dispenser, and the two substrates are bonded together under vacuum. Do. Then, both the substrates are sealed by irradiating the sealing agent part with ultraviolet rays using a high-pressure mercury lamp. Finally, the display element of the present invention is obtained by attaching polarizing plates to both outer surfaces of the liquid crystal cell.
上述の各表示素子の製造方法において使用される液晶としては、例えば、ネマティック型液晶、スメクティック型液晶等が挙げられる。また、液晶セルの外側に使用される偏光板としては、ポリビニルアルコールを延伸配向させながら、ヨウ素を吸収させた「H膜」と呼ばれる偏光膜を酢酸セルロース保護膜で挟んだ偏光板、又はH膜そのものからなる偏光板等が挙げられる。 Examples of the liquid crystal used in the above-described manufacturing method of each display element include nematic liquid crystal and smectic liquid crystal. In addition, as a polarizing plate used outside the liquid crystal cell, a polarizing film in which a polarizing film called an “H film” that absorbs iodine while stretching and aligning polyvinyl alcohol is sandwiched between cellulose acetate protective films, or an H film Examples thereof include a polarizing plate made of itself.
有機エレクトロルミネッセンス素子においては、当該感放射線性樹脂組成物から形成される硬化膜は、TFT素子上に形成される平坦化膜、発光部位を分ける隔壁材料等として使用できる。 In the organic electroluminescence element, the cured film formed from the radiation-sensitive resin composition can be used as a planarization film formed on the TFT element, a partition material that separates the light emitting sites, and the like.
以下、本発明を実施例に基づいて具体的に説明するが、本発明は、これらの実施例に限定されるものではない。各物性値の測定方法を下記に示す。
[重量平均分子量(Mw)及び数平均分子量(Mn)]
下記条件下、ゲルパーミエーションクロマトグラフィー(GPC)により測定した。また、分散度(Mw/Mn)は、Mw及びMnの測定結果より算出した。
EXAMPLES Hereinafter, although this invention is demonstrated concretely based on an Example, this invention is not limited to these Examples. The measuring method of each physical property value is shown below.
[Weight average molecular weight (Mw) and number average molecular weight (Mn)]
It measured by gel permeation chromatography (GPC) under the following conditions. The degree of dispersion (Mw / Mn) was calculated from the measurement results of Mw and Mn.
装置:GPC−101(昭和電工製)
カラム:GPC−KF−801、GPC−KF−802、GPC−KF−803及びGPC−KF−804を結合
移動相:テトラヒドロフラン
カラム温度:40℃
流速:1.0mL/分
試料濃度:1.0質量%
試料注入量:100μL
検出器:示差屈折計
標準物質:単分散ポリスチレン
Apparatus: GPC-101 (made by Showa Denko)
Column: GPC-KF-801, GPC-KF-802, GPC-KF-803 and GPC-KF-804 are combined Mobile phase: Tetrahydrofuran Column temperature: 40 ° C
Flow rate: 1.0 mL / min Sample concentration: 1.0% by mass
Sample injection volume: 100 μL
Detector: Differential refractometer Standard material: Monodisperse polystyrene
<[A]成分の合成>
[合成例1](重合体(A−1)の合成)
冷却管及び攪拌機を備えたフラスコに、2,2’−アゾビス(2,4−ジメチルバレロニトリル)7質量部、ジエチレングリコールエチルメチルエーテル200質量部を仕込んだ。引き続きメタクリル酸10質量部、メタクリル酸1−ブトキシエチル50質量部、3−メタクリロイルオキシメチル−3−エチルオキセタン40質量部、メタクリル酸ヒドロキシエチル10質量部を仕込み窒素置換した後、ゆるやかに撹拌を始めた。溶液の温度を70℃に上昇させ、この温度を5時間保持し重合体(A−1)を含む重合体溶液を得た。重合体(A−1)のポリスチレン換算重量平均分子量(Mw)は10,000であった。また、ここで得られた重合体溶液の固形分濃度は、31.6質量%であった。
<Synthesis of [A] Component>
[Synthesis Example 1] (Synthesis of polymer (A-1))
A flask equipped with a condenser and a stirrer was charged with 7 parts by mass of 2,2′-azobis (2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol ethyl methyl ether. Subsequently, 10 parts by weight of methacrylic acid, 50 parts by weight of 1-butoxyethyl methacrylate, 40 parts by weight of 3-methacryloyloxymethyl-3-ethyloxetane and 10 parts by weight of hydroxyethyl methacrylate were substituted with nitrogen, and then gently stirring was started. It was. The temperature of the solution was raised to 70 ° C., and this temperature was maintained for 5 hours to obtain a polymer solution containing the polymer (A-1). The polymer (A-1) had a weight average molecular weight (Mw) in terms of polystyrene of 10,000. Moreover, the solid content concentration of the polymer solution obtained here was 31.6 mass%.
[合成例2](重合体(A−2)の合成)
冷却管及び攪拌機を備えたフラスコに、2,2’−アゾビス(2,4−ジメチルバレロニトリル)7質量部、ジエチレングリコールエチルメチルエーテル200質量部を仕込んだ。引き続きメタクリル酸10質量部、テトラヒドロ−2H−ピラン−2−イルメタクリレート40質量部、メタクリル酸グリシジル40質量部、スチレン10質量部を仕込み窒素置換した後、ゆるやかに撹拌を始めた。溶液の温度を70℃に上昇させ、この温度を5時間保持し重合体(A−2)を含む重合体溶液を得た。重合体(A−2)のポリスチレン換算重量平均分子量(Mw)は9,500であった。また、ここで得られた重合体溶液の固形分濃度は、31.6質量%であった。
[Synthesis Example 2] (Synthesis of polymer (A-2))
A flask equipped with a condenser and a stirrer was charged with 7 parts by mass of 2,2′-azobis (2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol ethyl methyl ether. Subsequently, 10 parts by weight of methacrylic acid, 40 parts by weight of tetrahydro-2H-pyran-2-yl methacrylate, 40 parts by weight of glycidyl methacrylate, and 10 parts by weight of styrene were charged and purged with nitrogen, and then gently stirred. The temperature of the solution was raised to 70 ° C., and this temperature was maintained for 5 hours to obtain a polymer solution containing the polymer (A-2). The polystyrene equivalent weight average molecular weight (Mw) of the polymer (A-2) was 9,500. Moreover, the solid content concentration of the polymer solution obtained here was 31.6 mass%.
[合成例3](重合体(A−3)の合成)
冷却管及び攪拌機を備えたフラスコに、2,2’−アゾビス(2,4−ジメチルバレロニトリル)7質量部、ジエチレングリコールエチルメチルエーテル200質量部を仕込んだ。引き続きテトラヒドロ−2H−ピラン−2−イルメタクリレート40質量部、3,4−エポキシシクロヘキシルメチルメタアクリレート40質量部、メタクリル酸ヒドロキシエチル10質量部、スチレン10質量部を仕込み窒素置換した後、ゆるやかに撹拌を始めた。溶液の温度を70℃に上昇させ、この温度を5時間保持し重合体(A−3)を含む重合体溶液を得た。重合体(A−3)のポリスチレン換算重量平均分子量(Mw)は11,000であった。また、ここで得られた重合体溶液の固形分濃度は、32.4質量%であった。
[Synthesis Example 3] (Synthesis of Polymer (A-3))
A flask equipped with a condenser and a stirrer was charged with 7 parts by mass of 2,2′-azobis (2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol ethyl methyl ether. Subsequently, 40 parts by mass of tetrahydro-2H-pyran-2-yl methacrylate, 40 parts by mass of 3,4-epoxycyclohexylmethyl methacrylate, 10 parts by mass of hydroxyethyl methacrylate, and 10 parts by mass of styrene were charged with nitrogen, and then gently stirred. Started. The temperature of the solution was raised to 70 ° C., and this temperature was maintained for 5 hours to obtain a polymer solution containing the polymer (A-3). The polymer (A-3) had a polystyrene equivalent weight average molecular weight (Mw) of 11,000. Moreover, the solid content concentration of the polymer solution obtained here was 32.4 mass%.
[合成例4](重合体(a−1)の合成)
冷却管及び攪拌機を備えたフラスコに、2,2’−アゾビス(2,4−ジメチルバレロニトリル)7質量部、ジエチレングリコールエチルメチルエーテル200質量部を仕込んだ。引き続きテトラヒドロ−2H−ピラン−2−イルメタクリレート50量部、メタクリル酸ベンジル35質量部、メタクリル酸ヒドロキシエチル15質量部を仕込み窒素置換した後、ゆるやかに撹拌を始めた。溶液の温度を70℃に上昇させ、この温度を5時間保持し重合体(a−1)を含む重合体溶液を得た。重合体(a−1)のポリスチレン換算重量平均分子量(Mw)は10,500であった。また、ここで得られた重合体溶液の固形分濃度は、31.8質量%であった。
[Synthesis Example 4] (Synthesis of polymer (a-1))
A flask equipped with a condenser and a stirrer was charged with 7 parts by mass of 2,2′-azobis (2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol ethyl methyl ether. Subsequently, 50 parts by weight of tetrahydro-2H-pyran-2-yl methacrylate, 35 parts by weight of benzyl methacrylate, and 15 parts by weight of hydroxyethyl methacrylate were charged and purged with nitrogen, and then gently stirring was started. The temperature of the solution was raised to 70 ° C., and this temperature was maintained for 5 hours to obtain a polymer solution containing the polymer (a-1). The polymer (a-1) had a weight average molecular weight (Mw) in terms of polystyrene of 10,500. Moreover, the solid content concentration of the polymer solution obtained here was 31.8 mass%.
[合成例5](重合体(a−2)の合成)
冷却管及び攪拌機を備えたフラスコに、2,2’−アゾビス(2,4−ジメチルバレロニトリル)7質量部、ジエチレングリコールエチルメチルエーテル200質量部を仕込んだ。引き続きメタクリル酸グリシジル40質量部、スチレン30質量部、メタクリル酸ベンジル30質量部を仕込み窒素置換した後、ゆるやかに撹拌を始めた。溶液の温度を70℃に上昇させ、この温度を5時間保持し重合体(a−2)を含む重合体溶液を得た。重合体(a−2)のポリスチレン換算重量平均分子量(Mw)は10,000であった。また、ここで得られた重合体溶液の固形分濃度は、32.0質量%であった。
[Synthesis Example 5] (Synthesis of polymer (a-2))
A flask equipped with a condenser and a stirrer was charged with 7 parts by mass of 2,2′-azobis (2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol ethyl methyl ether. Subsequently, 40 parts by mass of glycidyl methacrylate, 30 parts by mass of styrene, and 30 parts by mass of benzyl methacrylate were charged and purged with nitrogen, and then gently agitated. The temperature of the solution was raised to 70 ° C., and this temperature was maintained for 5 hours to obtain a polymer solution containing the polymer (a-2). The polymer (a-2) had a weight average molecular weight (Mw) in terms of polystyrene of 10,000. Moreover, the solid content concentration of the polymer solution obtained here was 32.0 mass%.
〔C〕成分の合成
[合成例6](C−1)
<式(2−1)の化合物: 1,3−ビス(メタアクリロイルオキシエチル)ウレアの合成>
冷却管と撹拌機を備えたフラスコに、2−メタアクリロイルオキシエチルイソシアネート10部およびテトラヒドロフラン30部を仕込んだ。引き続き蒸留水2部を仕込み、溶液の温度を40℃に上昇させ1時間緩やかに撹拌を行った。減圧留去によりテトラヒドロフラン、蒸留水を除去した後、エタノール50部より再結晶を行い、針状白色結晶を得た。 得られた化合物が1,3−ビス(メタアクリロイルオキシエチル)ウレア(C−1)であることを、溶媒として重DMSO、基準としてTMSを用いて、1H−NMRにより確認した。結果を以下に示す。ケミカルシフト(プロトン比、分裂);1.82(3H,s)、3.26(2H,q)、3.99(2H,t)、5.61(1H,s)、6.00(1H,s)、6.08(1H,t)。
[C] Synthesis of Component [Synthesis Example 6] (C-1)
<Synthesis of Compound of Formula (2-1): 1,3-bis (methacryloyloxyethyl) urea>
A flask equipped with a condenser and a stirrer was charged with 10 parts of 2-methacryloyloxyethyl isocyanate and 30 parts of tetrahydrofuran. Subsequently, 2 parts of distilled water was added, the temperature of the solution was raised to 40 ° C., and the mixture was gently stirred for 1 hour. Tetrahydrofuran and distilled water were removed by distillation under reduced pressure, followed by recrystallization from 50 parts of ethanol to obtain needle-like white crystals. It was confirmed by 1H-NMR that the obtained compound was 1,3-bis (methacryloyloxyethyl) urea (C-1) using heavy DMSO as a solvent and TMS as a reference. The results are shown below. Chemical shift (proton ratio, splitting); 1.82 (3H, s), 3.26 (2H, q), 3.99 (2H, t), 5.61 (1H, s), 6.00 (1H , S), 6.08 (1H, t).
[合成例7](C−2)
<式(2−2)の化合物: 1,3−ビス(アクリロイルオキシエチル)ウレアの合成>
冷却管と撹拌機を備えたフラスコに、2−アクリロイルオキシエチルイソシアネート10部、テトラヒドロフラン30部を仕込んだ。引き続き蒸留水2部を仕込み、40℃に上昇させ1時間緩やかに撹拌を行った。減圧留去によりテトラヒドロフラン、蒸留水を除去した後、エタノール50部より再結晶を行い、針状白色結晶を得た。得られた化合物が1,3−ビス(アクリロイルオキシエチル)ウレア(C−2)であることを、溶媒として重DMSO、基準としてTMSを用いて、1H−NMRにより確認した。結果を以下に示す。ケミカルシフト(プロトン比、分裂);3.25(2H,q)、4.02(2H,t)、5.62(1H,s)、6.06(1H,s)、6.14(1H,t)。
[Synthesis Example 7] (C-2)
<Synthesis of Compound of Formula (2-2): 1,3-bis (acryloyloxyethyl) urea>
A flask equipped with a condenser and a stirrer was charged with 10 parts of 2-acryloyloxyethyl isocyanate and 30 parts of tetrahydrofuran. Subsequently, 2 parts of distilled water was added, the temperature was raised to 40 ° C., and the mixture was gently stirred for 1 hour. Tetrahydrofuran and distilled water were removed by distillation under reduced pressure, followed by recrystallization from 50 parts of ethanol to obtain needle-like white crystals. It was confirmed by 1H-NMR that the obtained compound was 1,3-bis (acryloyloxyethyl) urea (C-2) using heavy DMSO as a solvent and TMS as a reference. The results are shown below. Chemical shift (proton ratio, splitting); 3.25 (2H, q), 4.02 (2H, t), 5.62 (1H, s), 6.06 (1H, s), 6.14 (1H , T).
[合成例8](C−3)
<式(2−3)の化合物:1,3−ビス(メタアクリロイルオキシ−2−エトキシエチル)ウレアの合成>
冷却管と撹拌機を備えたフラスコに、2−メタアクリロイルオキシ−2−エトキシエチルイソシアネート12部、テトラヒドロフラン30部を仕込んだ。引き続き蒸留水2部を仕込み、40℃に上昇させ1時間緩やかに撹拌を行った。減圧留去によりテトラヒドロフラン、蒸留水を除去し、無色液体を得た。得られた化合物が1,3−ビス(メタアクリロイルオキシ−2−エトキシエチル)ウレア(C−3)であることを、溶媒として重DMSO、基準としてTMSを用いて、1H−NMRにより確認した。結果を以下に示す。ケミカルシフト(プロトン比、分裂);1.87(3H,s)、3.36(2H,q)、3.62(2H,t)、3.75(2H,t)3.99(2H,t)、4.30(2H,t)5.63(1H,s)、5.94(1H,t)、6.01(1H,s)。
[Synthesis Example 8] (C-3)
<Synthesis of Compound of Formula (2-3): 1,3-bis (methacryloyloxy-2-ethoxyethyl) urea>
A flask equipped with a condenser and a stirrer was charged with 12 parts of 2-methacryloyloxy-2-ethoxyethyl isocyanate and 30 parts of tetrahydrofuran. Subsequently, 2 parts of distilled water was added, the temperature was raised to 40 ° C., and the mixture was gently stirred for 1 hour. Tetrahydrofuran and distilled water were removed by distillation under reduced pressure to obtain a colorless liquid. It was confirmed by 1H-NMR that the obtained compound was 1,3-bis (methacryloyloxy-2-ethoxyethyl) urea (C-3) using heavy DMSO as a solvent and TMS as a reference. The results are shown below. Chemical shift (proton ratio, splitting); 1.87 (3H, s), 3.36 (2H, q), 3.62 (2H, t), 3.75 (2H, t) 3.99 (2H, t), 4.30 (2H, t) 5.63 (1H, s), 5.94 (1H, t), 6.01 (1H, s).
[合成例9](C−4)
< 式(2−5)の化合物>
冷却管と撹拌機を備えたフラスコに、2−メタアクリロイルオキシエチルイソチオシアネート10部およびテトラヒドロフラン30部を仕込んだ。引き続き蒸留水2部を仕込み、溶液の温度を40℃に上昇させ1時間緩やかに撹拌を行った。減圧留去によりテトラヒドロフラン、蒸留水を除去した後、エタノール50部より再結晶を行い、針状白色結晶を得た。 得られた化合物が「式(2−5)の化合物」であることを、溶媒として重DMSO、基準としてTMSを用いて、1H−NMRにより確認した。結果を以下に示す。ケミカルシフト(プロトン比、分裂);1.80(3H,s)、3.22(2H,q)、3.91(2H,t)、5.58(1H,s)、6.02(1H,s)、6.02(1H,t)。
[Synthesis Example 9] (C-4)
<Compound of formula (2-5)>
A flask equipped with a condenser and a stirrer was charged with 10 parts of 2-methacryloyloxyethyl isothiocyanate and 30 parts of tetrahydrofuran. Subsequently, 2 parts of distilled water was added, the temperature of the solution was raised to 40 ° C., and the mixture was gently stirred for 1 hour. Tetrahydrofuran and distilled water were removed by distillation under reduced pressure, followed by recrystallization from 50 parts of ethanol to obtain needle-like white crystals. It was confirmed by 1H-NMR that the obtained compound was “compound of formula (2-5)” using heavy DMSO as a solvent and TMS as a reference. The results are shown below. Chemical shift (proton ratio, splitting); 1.80 (3H, s), 3.22 (2H, q), 3.91 (2H, t), 5.58 (1H, s), 6.02 (1H) , S), 6.02 (1H, t).
<感放射線性樹脂組成物の調製>
感放射線性樹脂組成物の調製に用いた[B]光酸発生剤、[C]化合物及び[D]環状エーテル基を有する化合物、[E]酸化防止剤、[E]塩基性化合物を以下に示す。
<Preparation of radiation-sensitive resin composition>
The [B] photoacid generator, [C] compound and [D] compound having a cyclic ether group, [E] antioxidant, and [E] basic compound used for the preparation of the radiation sensitive resin composition are as follows. Show.
[[B]光酸発生剤]
B−1:5−プロピルスルフォニルオキシイミノ−5H−チオフェン−2−イリデン)−(2−メチルフェニル)アセトニトリル(IRGACURE PAG 103、BASF製)
B−2:(5−p−トルエンスルフォニルオキシイミノ−5H−チオフェン−2−イリデン)−(2−メチルフェニル)アセトニトリル(IRGACURE PAG 121、BASF製)
B−3:(5−オクチルスルフォニルオキシイミノ)−(4−メトキシフェニル)アセトニトリル(CGI−725、BASF製)
B−4:下記式(8)で示されるオキシムエステル化合物(IRGACURE PAG 203、BASF製)
[[B] Photoacid generator]
B-1: 5-propylsulfonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl) acetonitrile (IRGACURE PAG 103, manufactured by BASF)
B-2: (5-p-toluenesulfonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl) acetonitrile (IRGACURE PAG 121, manufactured by BASF)
B-3: (5-octylsulfonyloxyimino)-(4-methoxyphenyl) acetonitrile (CGI-725, manufactured by BASF)
B-4: Oxime ester compound represented by the following formula (8) (IRGACURE PAG 203, manufactured by BASF)
B−5:N−ヒドロキシナフタルイミド−トリフルオロメタンスルホン酸エステル
B-5: N-hydroxynaphthalimide-trifluoromethanesulfonic acid ester
[[C]化合物]
C−1: 式(2−1)の化合物得 1,3−ビス(メタアクリロイルオキシエチル)ウレア
C−2: 式(2−2)の化合物得 1,3−ビス(アクリロイルオキシエチル)ウレア
C−3: 式(2−3)の化合物得 1,3−ビス(メタアクリロイルオキシ−2−エトキシエチル)ウレア
C−4:式(2−5)の化合物
[[C] Compound]
C-1: Compound of formula (2-1) 1,3-bis (methacryloyloxyethyl) urea C-2: Compound of formula (2-2) 1,3-bis (acryloyloxyethyl) urea C -3: Compound of formula (2-3) 1,3-bis (methacryloyloxy-2-ethoxyethyl) urea C-4: Compound of formula (2-5)
[[D]環状エーテル基を有する化合物]
D−1:イソフタル酸=ビス[(3−エチルオキセタン−3−イル)メチル]
D−2:1,4−ビス[(3−エチルオキセタン−3−イル)メトキシメチル]ベンゼン
[[D] Compound having cyclic ether group]
D-1: Isophthalic acid = bis [(3-ethyloxetane-3-yl) methyl]
D-2: 1,4-bis [(3-ethyloxetane-3-yl) methoxymethyl] benzene
[[E]酸化防止剤]
E−1:ペンタエリスリトールテトラキス[3−(3,5−ジ-tert-ブチル−4−ヒドロキシフェニル)プロピオネート](アデカスタブAO−60、アデカ製)
E−2:トリス−(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)−イソシアヌレイト(アデカスタブAO−20、アデカ製)
[[E] Antioxidant]
E-1: Pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (ADK STAB AO-60, manufactured by ADEKA)
E-2: Tris- (3,5-di-tert-butyl-4-hydroxybenzyl) -isocyanurate (ADK STAB AO-20, manufactured by ADEKA)
[[F]塩基性化合物]
F−1:4−ジメチルアミノピリジン
[[F] basic compound]
F-1: 4-Dimethylaminopyridine
[実施例1]
[A]重合体成分としての(A−1)を含む重合体溶液((A−1)100質量部(固形分)に相当する量)に、[B]光酸発生剤としての(B−1)3質量部、[C]化合物としての(C−1)10質量部を混合し、孔径0.2μmのメンブランフィルタで濾過することにより、感放射線性樹脂組成物を調製した。表1に示す。
[Example 1]
[A] To a polymer solution containing (A-1) as a polymer component (amount corresponding to 100 parts by mass (solid content) of (A-1)), [B] (B- 1) 3 parts by mass and 10 parts by mass of (C-1) as a [C] compound were mixed and filtered through a membrane filter having a pore size of 0.2 μm to prepare a radiation-sensitive resin composition. Table 1 shows.
[実施例2〜5及び比較例1〜2]
下記表1に示す種類及び配合量の各成分を用いた以外は、実施例1と同様に操作し、各感放射線性樹脂組成物を調製した。なお、表1中の「−」は、該当する成分を配合しなかったことを示す。
[Examples 2-5 and Comparative Examples 1-2]
Except having used each component of the kind and compounding quantity shown in following Table 1, it operated similarly to Example 1 and prepared each radiation sensitive resin composition. In addition, "-" in Table 1 indicates that the corresponding component was not blended.
[実施例6及び比較例3]
(a−1)を含む重合体溶液((a−1)50質量部(固形分)に相当する量)と、(a−2)を含む重合体溶液((a−2)50質量部(固形分)に相当する量)とを混合して[A]重合体成分とし、これに[B]光酸発生剤としての(B−2)3質量部、[C]化合物としての(C−1)10質量部を混合し、次いで、孔径0.2μmのメンブランフィルタで濾過することにより、感放射線性樹脂組成物を調製した。表1に示す。
[実施例7]
下記表1に示す種類及び配合量の各成分を用いた以外は、実施例6と同様に操作し、各感放射線性樹脂組成物を調製した。表1に示す。
[Example 6 and Comparative Example 3]
A polymer solution containing (a-1) (an amount corresponding to 50 parts by mass (solid content) of (a-1)) and a polymer solution containing (a-2) (50 parts by mass of (a-2) ( The amount corresponding to the solid content) is mixed to obtain [A] a polymer component, and [B] 3 parts by mass of (B-2) as a photoacid generator and (C-) as a [C] compound. 1) 10 parts by mass was mixed, and then filtered through a membrane filter having a pore size of 0.2 μm to prepare a radiation sensitive resin composition. Table 1 shows.
[Example 7]
Except having used each component of the kind and compounding quantity shown in following Table 1, it operated similarly to Example 6 and prepared each radiation sensitive resin composition. Table 1 shows.
<評価>
調製した各感放射線性樹脂組成物を用い、下記の評価を実施した。結果を表1に示す。
[感度(J/m2)]
ガラス基板上に、各感放射線性樹脂組成物溶液をスピンナを用いて塗布した後、90℃にて2分間ホットプレート上でプレベークして膜厚3.0μmの塗膜を形成した。続いて、露光機(MPA−600FA、ghi線混合、キヤノン製)を用い、60μmのライン・アンド・スペース(10対1)のパターンを有するマスクを介して、塗膜に対し露光量を変量として放射線を照射した。その後、0.5質量%のテトラメチルアンモニウムヒドロキシド水溶液にて25℃において80秒間液盛り法で現像した。次いで、超純水で1分間流水洗浄を行い、その後乾燥することにより、HMDS処理後のクロム成膜ガラス基板上にパターンを形成した。このとき、6μmのスペース・パターンが完全に溶解するために必要な露光量を調べた。この露光量の値が500(J/m2)以下の場合、感度は良好と判断できる。
[耐光性の評価]
シリコン基板上に、各感放射線性樹脂組成物溶液をスピンナを用いて塗布した後、90℃にて2分間ホットプレート上でプレベークして膜厚3.0μmの塗膜を形成した。このシリコン基板をクリーンオーブン内にて220℃で1時間加熱して硬化膜を得た。得られた各硬化膜に、UV照射装置(ウシオ社製の「UVX−02516S1JS01」)にて130mWの照度で800000J/m2照射した。照射前の膜厚に比較して、照射後の膜厚の膜減り量が3%以下であれば硬化膜の耐光性が良好であると言える。
<Evaluation>
The following evaluation was implemented using each prepared radiation sensitive resin composition. The results are shown in Table 1.
[Sensitivity (J / m 2 )]
Each radiation sensitive resin composition solution was applied on a glass substrate using a spinner, and then pre-baked on a hot plate at 90 ° C. for 2 minutes to form a coating film having a thickness of 3.0 μm. Subsequently, using an exposure machine (MPA-600FA, ghi line mixing, manufactured by Canon), the exposure amount was changed to the coating film through a mask having a 60 μm line and space (10 to 1) pattern. Irradiated. Then, it developed by the piling method for 80 seconds at 25 degreeC with 0.5 mass% tetramethylammonium hydroxide aqueous solution. Next, washing with running ultrapure water for 1 minute was performed, followed by drying to form a pattern on the chromium-deposited glass substrate after the HMDS treatment. At this time, the amount of exposure necessary to completely dissolve the 6 μm space pattern was examined. When the exposure value is 500 (J / m 2 ) or less, it can be determined that the sensitivity is good.
[Evaluation of light resistance]
Each radiation sensitive resin composition solution was applied onto a silicon substrate using a spinner and then pre-baked on a hot plate at 90 ° C. for 2 minutes to form a coating film having a thickness of 3.0 μm. This silicon substrate was heated in a clean oven at 220 ° C. for 1 hour to obtain a cured film. Each obtained cured film was irradiated with 800,000 J / m 2 at an illuminance of 130 mW with a UV irradiation apparatus (“UVX-02516S1JS01” manufactured by USHIO Co., Ltd.). It can be said that the light resistance of the cured film is good when the amount of film thickness reduction after irradiation is 3% or less compared to the film thickness before irradiation.
尚、耐光性の評価においては、形成する硬化膜のパターニングは不要のため、現像工程は省略し、塗膜形成工程、耐光性試験および加熱工程のみ行い評価を行った。
[透過率の評価]
上記耐光性の評価と同様に、シリコン基板上に塗膜を形成した。このシリコン基板をクリーンオーブン内にて220℃で1時間加熱して硬化膜を形成した。得られた各硬化膜について、波長400nmにおける透過率を、分光光度計(日立製作所社製の「150−20型ダブルビーム」)を用いて測定して評価した。このとき、90%未満の場合に透明性が不良と言える。
In the evaluation of light resistance, patterning of the cured film to be formed is unnecessary, and therefore the development process was omitted, and only the coating film forming process, the light resistance test, and the heating process were performed for evaluation.
[Evaluation of transmittance]
A coating film was formed on a silicon substrate in the same manner as the light resistance evaluation. This silicon substrate was heated in a clean oven at 220 ° C. for 1 hour to form a cured film. About each obtained cured film, the transmittance | permeability in wavelength 400nm was measured and evaluated using the spectrophotometer ("150-20 type double beam" by Hitachi, Ltd.). At this time, if it is less than 90%, it can be said that the transparency is poor.
[パターン形状の熱安定性の評価観察]
感度の評価で形成したパターンが形成された基板をクリーンオーブン内にて230℃で1時間追加加熱して、形成したパターンをSEM(走査電子顕微鏡)で形状を観察した。
追加加熱により、パターン形状が矩形形状からドーム形状にメルトフローした場合、パターン形状の熱安定性が不良と判断した。判断基準を以下に示す。
メルトフローによるパターン形状の変形がほとんど見られない場合: 「○」、
メルトフローによるパターン形状の変形が見られた場合: 「△」
メルトフローによりパターン形状が大きく変形した場合: 「×」
[Evaluation observation of thermal stability of pattern shape]
The substrate on which the pattern formed by the sensitivity evaluation was formed was additionally heated in a clean oven at 230 ° C. for 1 hour, and the shape of the formed pattern was observed with an SEM (scanning electron microscope).
When the pattern shape melt-flowed from the rectangular shape to the dome shape by additional heating, the thermal stability of the pattern shape was judged to be poor. Judgment criteria are shown below.
When there is almost no deformation of the pattern shape due to melt flow: “○”,
When pattern deformation due to melt flow is observed: “△”
When pattern shape is greatly deformed by melt flow: “×”
[露光引き置き後のパターンの密着性の評価]
ガラス基板上に、各感放射線性樹脂組成物溶液をスピンナを用いて塗布した後、90℃にて2分間ホットプレート上でプレベークして膜厚3.0μmの塗膜を形成した。続いて、露光機(MPA−600FA、ghi線混合、キヤノン製)を用い、10μmのライン・アンド・スペース(1対1)のパターンを有するマスクを介して、700(J/m2)の露光量で露光した。その後、1時間クリーンルーム内で放置し、その後0.5質量%のテトラメチルアンモニウムヒドロキシド水溶液にて25℃において80秒間液盛り法で現像した。次いで、超純水で1分間流水洗浄を行い、その後乾燥し、ガラス基板上にパターンを形成した。現像後基板を光学顕微鏡で観察し、パターンの剥がれの有無を確認した。パターンの剥がれ見られない場合、密着性良好と判断できる。
判断基準を以下に示す。
パターン剥がれがほとんど見られない場合: 「○」、
パターン剥がれがわずかに見られた場合: 「△」
パターンが剥がれ、基板上にパターンがほとんど残っていない場合: 「×」
とした。結果を表1に示す。
[Evaluation of adhesion of pattern after exposure]
Each radiation sensitive resin composition solution was applied on a glass substrate using a spinner, and then pre-baked on a hot plate at 90 ° C. for 2 minutes to form a coating film having a thickness of 3.0 μm. Subsequently, using an exposure machine (MPA-600FA, mixed ghi line, manufactured by Canon), exposure of 700 (J / m 2 ) is performed through a mask having a 10 μm line-and-space (one-to-one) pattern. Exposed in quantity. Thereafter, it was left in a clean room for 1 hour, and then developed with a 0.5 mass% aqueous solution of tetramethylammonium hydroxide at 25 ° C. for 80 seconds. Next, running water was washed with ultrapure water for 1 minute, and then dried to form a pattern on the glass substrate. After development, the substrate was observed with an optical microscope to confirm the presence or absence of pattern peeling. If the pattern is not peeled off, it can be determined that the adhesion is good.
Judgment criteria are shown below.
When pattern peeling is hardly seen: “○”,
When pattern peeling is slightly seen: “△”
When the pattern is peeled off and almost no pattern remains on the substrate: “×”
It was. The results are shown in Table 1.
表1の結果から明らかなように、当該感放射線性樹脂組成物は、感度に優れ、硬化膜として評価した場合、透過率、耐光性、パターン形状の熱安定性に優れるとともに、露光引き置き後のパターンの密着性に優れていることがわかった。
As is apparent from the results in Table 1, the radiation-sensitive resin composition is excellent in sensitivity and, when evaluated as a cured film, is excellent in transmittance, light resistance, and thermal stability of the pattern shape, and after exposure to exposure. It was found that the adhesion of the pattern was excellent.
Claims (10)
[B]光酸発生剤
[C]下記式(1)で示される化合物を含有する感放射線性樹脂組成物。
(式(1)において、Xは酸素原子または硫黄原子を示し、R1、R2はそれぞれ独立に、単結合または2から4価の有機基を示し、R3、R4はそれぞれ独立に、不飽和複素環基、炭素数11〜20のアルキル基、オキシラニル基、オキセタニル基、ビニル基、(メタ)アクリロイルオキシ基、水酸基、カルボキシル基、アルコキシシリル基、メルカプト基、スルホ基を示す。n,mはそれぞれ独立に1から3の整数を示す。) [A] Polymer component containing structural unit (I) containing an acid dissociable group and structural unit (II) containing a crosslinkable group in the same or different polymers, and [B] photoacid generator [C] The radiation sensitive resin composition containing the compound shown by Formula (1).
(In Formula (1), X represents an oxygen atom or a sulfur atom, R 1 and R 2 each independently represents a single bond or a divalent to tetravalent organic group, and R 3 and R 4 each independently represent An unsaturated heterocyclic group, an alkyl group having 11 to 20 carbon atoms, an oxiranyl group, an oxetanyl group, a vinyl group, a (meth) acryloyloxy group, a hydroxyl group, a carboxyl group, an alkoxysilyl group, a mercapto group, and a sulfo group. m represents an integer of 1 to 3 independently.)
(式(2)において、Xは酸素原子または硫黄原子を示し、R1、R2はそれぞれ独立に、単結合または2から4価の有機基を示し、R5、R6はそれぞれ独立に、水素原子、メチルを示す。n,mはそれぞれ独立に1から3の整数を示す。) The radiation-sensitive resin composition according to claim 1, wherein the [C] is a compound represented by the following formula (2).
(In Formula (2), X represents an oxygen atom or a sulfur atom, R 1 and R 2 each independently represent a single bond or a divalent to tetravalent organic group, and R 5 and R 6 each independently represent A hydrogen atom and methyl, n and m each independently represent an integer of 1 to 3)
(式(3)中、R7は、水素原子又はメチル基を示す。R8は、炭素数1〜12のアルキル基であり、R9は、炭素数1〜12のアルキル基又は炭素数4〜20の1価の脂環式炭化水素基を示す。
式(4)中、R10は、水素原子又はメチル基を示す。R11からR17は、それぞれ独立して、水素原子又は炭素数1〜12のアルキル基である。aは、1又は2の整数であり、aが2の場合、複数のR16及びR17は、それぞれ同一でも異なっていてもよい。 The structural unit (I) containing the acid dissociable group of [A] is at least one selected from a structural unit represented by the following formula (3) and a structural unit represented by the following formula (4): The radiation sensitive resin composition as described in any one of Claim 1 or Claim 2.
(In Formula (3), R 7 represents a hydrogen atom or a methyl group. R 8 is an alkyl group having 1 to 12 carbon atoms, and R 9 is an alkyl group having 1 to 12 carbon atoms or 4 carbon atoms. -20 monovalent alicyclic hydrocarbon groups are shown.
In formula (4), R 10 represents a hydrogen atom or a methyl group. R 11 to R 17 are each independently a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. a is an integer of 1 or 2, and when a is 2, a plurality of R 16 and R 17 may be the same or different.
(式(5)中、R18は、アルキル基、脂環式炭化水素基、アリール基、又はこれらのアルキル基、脂環式炭化水素基及びアリール基が有する水素原子の一部又は全部が置換基で置換された基である。) [B] The radiation-sensitive resin composition according to any one of claims 1 to 5, wherein the photoacid generator contains an oxime sulfonate group represented by the following formula (5).
(In the formula (5), R 18 is an alkyl group, an alicyclic hydrocarbon group, an aryl group, or a part or all of the hydrogen atoms of the alkyl group, alicyclic hydrocarbon group, and aryl group are substituted. A group substituted with a group.)
(2)上記塗膜の少なくとも一部に放射線を照射する工程、
(3)上記放射線が照射された塗膜を現像する工程、及び
(4)上記現像された塗膜を加熱する工程
を有する硬化膜の形成方法。 (1) The process of forming a coating film on a board | substrate using the radiation sensitive resin composition as described in any one of Claims 1-7,
(2) A step of irradiating at least a part of the coating film with radiation,
(3) The process of developing the coating film irradiated with the said radiation, (4) The formation method of the cured film which has the process of heating the said developed coating film.
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